Simple exploration of 187973-60-0

The synthetic route of 187973-60-0 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.187973-60-0,6-Iodopyridazin-3-amine,as a common compound, the synthetic route is as follows.

General procedure: A 10 mL round-bottomed flask containing a magnetic stirbar was charged with CuI (0.1 mmol) followed by L-hydroxyproline (0.2 mmol),6-iodopyridazin-3-amine (1.3 mmol) and K3PO4 (3.0 mmol). The flask wasflushed with N2 and a solution of the appropriate amine (1.0 mmol) inanhydrous DMSO (1.5 mL) was then added. The mixture was stirred under N2at 50 C for 24 h. MeOH (5 mL) and H2O (5 mL) were added and the stirredmixture was neutralised by dropwise addition of AcOH. The resultant solidswere allowed to settle out and the supernatant solution added to the top of astrong cation exchange (SCX) column. The remaining solid was washed withfurther MeOH (5 mL), and the washings also added to the SCX column. Thesolution was allowed to elute slowly through the column, which was thenflushed with further MeOH. These MeOH washings were discarded. A 1 Msolution of NH3 in MeOH was flushed through until elution of the product wascomplete and the solvent was evaporated under reduced pressure to yield acrude material. Purification was done by flash silica chromatography, elutiongradient typically 0-10% MeOH in CH2Cl2. Relevant fractions were evaporatedto dryness to afford the desired product., 187973-60-0

The synthetic route of 187973-60-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Bethel, Paul A.; Roberts, Bryan; Bailey, Andrew; Tetrahedron Letters; vol. 55; 37; (2014); p. 5186 – 5190;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

Analyzing the synthesis route of 19064-65-4

19064-65-4, As the paragraph descriping shows that 19064-65-4 is playing an increasingly important role.

19064-65-4, 3-Methoxypyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

b) 3-Methoxy-4-(tributylstannyl)pyridazine n-Butyllithium (7.1 mL of a 2.5 M solution in hexanes, 17.75 mmol) was slowly added (0.2 mL/min) to a solution of 2,2,6,6-tetramethylpiperidine (3 mL, 17,75 mmol) in dry diethyl ether (16 mL) at -30 ?C under argon atmosphere. The reaction mixture was stirred at 0 ?C for 30 minutes before being cooled down to -78 ?C and a solution of 3-methoxypyridazine (0.85 g, 7.72 mmol) in dry diethyl ether (4 mL) was slowly added (0.03 mL/min). The reaction mixture was stirred at this temperature for 10 additional minutes before the addition of tributylchlorostannane (2.5 mL, 9.22 mmol). After stirring at -78 ?C for 45 minutes, a mixture of diethyl ether and aqueous saturated solution of ammonium chloride (15 mL/15 mL) was added and the temperature was allowed to warm up to room temperature. Additional diethyl ether (300 mL) was then added to the mixture and the organic layer was separated, washed with saturated aqueous solution of ammonium chloride, dried over magnesium sulphate and the solvent removed under reduced pressure. The residue was purified by flash chromatography (100% hexanes to 1:1 hexanes/diethyl ether) to give the title compound (0.31 g, 10%) as a pale yellow oil. 1H-NMR delta (300 MHz, CDCl3): 0.88 (t, 9H), 1.03 – 1.19 (m, 6H), 1.23 – 1.40 (m, 6H), 1.43 – 1.61 (m, 6H), 4.09 (s, 3H), 7.44 (d, 1H), 8.69 (d, 1H).

19064-65-4, As the paragraph descriping shows that 19064-65-4 is playing an increasingly important role.

Reference£º
Patent; Almirall, S.A.; EP2463289; (2012); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

Downstream synthetic route of 932-22-9

932-22-9 4,5-Dichloro-3(2H)-pyridazinone 73247, apyridazine compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.932-22-9,4,5-Dichloro-3(2H)-pyridazinone,as a common compound, the synthetic route is as follows.,932-22-9

General procedure: To a solutionof 4,5-dichloropyridazin-3(2H)-one (1, 3.0 mmol) andEt3N (3.6 mmol) in CH2Cl2 (30 mL) was added dropwise theappropriate alkyl/aryl chloroformate (2, 3.9 mmol) and themixture was stirred for 10 min at 5 C (Scheme 1). Thereaction mixture was washed using water (5 ¡Á 50 mL). Theorganic layer was dried over anhydrous magnesium sulfate,and then evaporated under reduced pressure. The resultingresidue was recrystallized from THF/n-hexane (1:3, v/v) togive the product 3.

932-22-9 4,5-Dichloro-3(2H)-pyridazinone 73247, apyridazine compound, is more and more widely used in various fields.

Reference£º
Article; Sung, Gi Hyeon; Bo, Ram Kim; Ryu, Ki Eun; Kim, Jeum-Jong; Yoon, Yong-Jin; Bulletin of the Korean Chemical Society; vol. 35; 9; (2014); p. 2758 – 2764;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

New learning discoveries about 289-80-5

The synthetic route of 289-80-5 has been constantly updated, and we look forward to future research findings.

289-80-5, Pyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of pyridazine (3.63 mL, 49.9 mmol) in DCM (60 mL) was added trimethylsilyl cyanide (11.99 mL, 90 mmol) and aluminium chloride (20 mg, 0.150 mmol). After stirring the reaction mixture at room temperature for 10 minutes, a solution of para-toluene sulfonyl chloride (16.38 mL, 86 mmol) in DCM (100 mL) was added dropwise via an addition funnel over 30 minutes. The resulting light orange solution was left stirring at room temperature overnight. The reaction mixture was concentrated to give a light brown solid. To this material was added EtOH (100 mL). A white precipitate crashed out which was filtered through a sintered funnel. The precipitate was washed with ethanol and collected. LC3 rt = 1.4 min, m/z = 262 (M+H)., 289-80-5

The synthetic route of 289-80-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Merck Sharp & Dohme Corp.; BROCKUNIER, Linda, L.; GUO, Jian; PARMEE, Emma, R.; RAGHAVAN, Subharekha; ROSAUER, Keith; STELMACH, John, E.; SCHMIDT, Darby Rye; (87 pag.)EP2373317; (2016); B1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

Brief introduction of 14161-11-6

14161-11-6, The synthetic route of 14161-11-6 has been constantly updated, and we look forward to future research findings.

14161-11-6, 3,4,5-Trichloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

47.93 g (0.261 mole) of 3,4,5-trichloro-pyridazine are dissolved in ethanol and 49.7 ml (r=0.982 g/cm3, 0.65 mole) of 3-amino-1-propanol are added to it under stirring. The solution is heated to boiling, boiled for 30 minutes and a sample is taken for TLC (eluent: a 10:10:0.5 mixture of ethyl acetate:acetone:triethylamine, Rf values: (XI)=0.90, (IV)=0.48, (IVA)=0.32, contamination of unknown stucture=0.75). The reaction takes place generally within 30 minutes and 1 hour, the whole amount of the starting substance is used up. The reaction mixture is then evaporated, 13 g of sodium chloride are dissolved in distilled water and the thus-obtained solution is added to the evaporated mixture under stirring. The reaction mixture is allowed to stand in a refrigerator overnight at 5 C. The separated crystals are washed with 10 to 12 ml of cold distilled water and the precipitate is dried. Thus 27.7 g (47.7%) of crude product (IVA) are obtained. M.p.: 150-153 C. After recrystallization from methanol the melting point rises to 157-158 C. The physical characteristics will be specified later. [00051] The aqueous mother liquor is extracted 5 times with 200 cm3 each of ethyl acetate, dried over hot magnesium sulfate, filtered on activated carbon and evaporated to dry. The bulk of the residual crude product is the compound of formula (IV). [00052] Yield of the crude product: 28.02 g (48.32%), according to HPLC analysis it contains 7 to 8% of (IVA) and 1 to 2% of contamination of unknown structure. The crude product is purified by recrystallization from cold diethyl ether in the following way: 300 ml of diethyl ether are added to it in 5 portions and the oily product is stirred at room temperature. The ether solution is decanted on every occasion and fresh ether is used. The ether solutions are combined, evaporated to a volume of 100 ml and the separated crystals are filtered off. Thus 15.6 g (26%) of compound of the formula (IV) are obtained. M.p.: 65-66 C. According to MPLC analysis carried out after purification (IVA) <3.0% and (IV)>97%. For the elaboration of the HPLC method small amounts of standards have been prepared by column chromatography. HPLC method: [00053] Column: Ultrasphere SI 3 mm. 75 cm¡Á4.6 mm. [00054] Eluent: cyclohexane:ethyl acetate (1:1). [00055] Flow rate: 1.0 ml/min. [00056] Detection: UV 254 nm. [00057] Injected volume: 20 ml (0.8% dilution). [00058] Retention times: 5.13 for compound (IV) and 13.46 minutes for compound (IVA).The Physico-chemical Characteristics of 4-(3-hydroxypropyl-amino)-3,5-dichloropyridazine (IV) [00059] M.p.: 65-66 C. [00060] TLC: ethyl acetate_triethylamine=20:0.5 [00061] Rf=0.36[TABLE-US-00001] Analysis for the formula C7H9Cl2NO3 (222.08): CHClN Calculated: 37.86%4.09%31.93%18.92% Found: 37.624.12%31.71%18.67% IR (KRr) nu cm-1: 3249, 2947, 1591, 1454, 1390, 1353, 1212, 1177, 1124, 1075, 1037, 908, 683, 522, 460. [00062] 1H-NMR (DMSO): delta 8.70 [s, (1H) pyridazine C-6 ], 6.8 [t, (1H) 4-NH], 4.7 [t, (1H) OH], 3.74 [qa, (2H) N-CH 2], 3.5 [qa, (2H) CH2-O-] 1.73 [m, (2H) C-CH2-C]. [00063] 13CNMR (DMSO) delta ppm: 150.8, 116.0, 140.1, 114.7 (pyridazine carbon atoms), (60 C-OH), (43.6 NH-C), (31.9 C-CH2-C).Physico-chemical Characteristics of the 5-(3-hydroxypropyl-amino)-3.4-dichloropyridazine (IVA) [00064] M.p.: 157-158 C. [00065] TLC: ethyl acetate_triethylamine=20:0.5 [00066] Rf=0.16[TABLE-US-00002] Analysis for the formula C7H9Cl2N3O (222.08): CHClN Calculated: 37.86%4.09%31.93%18.92% Found: 37.684.11%31.77%18.73% IR (KBr) nu cm-1: 3269, 2935, 1568, 1334, 1283, 1224, 1139, 1070, 1043, 861, 830, 795, 661, 540, 514. [00067] 1H-NMR (DMSO): delta ppm: 8.73 [s,(1H) pyridazine C-6], 7.59 [t,(1H) 5-NH], 4.66 [t,(1H) OH], 3.4-3.6 [m,(4H) CH2-X X=heteroatom], 1.73 [m,(2H) C-CH2C]. [00068] The stereoscopic vicinity of the NH proton at position 5 and the pyridazine proton at position 6 has been proved by a DNOE experiment. [00069] 13CNMR (DMSO) delta ppm: 152.1, 143.7, 137.2, 114.4 (pyridazine carbon atoms), (58.4 C-OH), (39.9 C-NH), (31.4 C-CH2-C).

14161-11-6, The synthetic route of 14161-11-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Egis Gyogyszergyar Rt.; US6800758; (2004); B1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

Brief introduction of 7252-84-8

As the paragraph descriping shows that 7252-84-8 is playing an increasingly important role.

7252-84-8,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.7252-84-8,3-Amino-6-methoxypyridazine,as a common compound, the synthetic route is as follows.

Example 67: Preparation of 2-{3-[2-(4-chlorophenyl)ethyl]-l-(4-fluorophenyl)-5- oxo-2-sulfanylideneimia^zolidin-4-yl}-N-(5-methoxypyridin-2-yl)acetamMe. TBTU (18.2 mg; 0.55 mmol; 1.5 eq) and DIPEA (129 mu 0.74 mmol; 2 eq) were added to a solution of 2-{3-[2-(4-chlorophenyl)ethyl]-l-(4-fluorophenyl)-5-oxo-2- sulfanylideneimidazolidin-4-yl} acetic acid (1-5) (150 mg; 0.37 mmol; 1 eq) in dioxane (2 mL). The reaction mixture was stirred at room temperature for 30 minutes, before adding 6-methoxypyridazin-3-amine (93 mg; 0.74 mmol; 2 eq) in dimethylformamide (0.1 mL). The reaction mixture was stirred at room temperature overnight. Saturated ammonium chloride (30 mL) was added and the aqueous layer was extracted with ethyl acetate (3 x 30 mL). The combined organic layers were washed with saturated sodium chloride (3 x 30 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude was triturated in methanol/diethyl ether. The title compound, 2-{3-[2-(4-chlorophenyl)ethyl]-l-(4- fluorophenyl)-5-oxo-2-sulfanylideneimidazolidin-4-yl}-N-(5-methoxypyridin-2- yl)acetamide was obtained in 17% yield (33.14 mg) as a white powder. 1H-NMR (DMSO-d6): delta (ppm) 2.9 (m, 1H), 3.04 (m, 1H), 3.22 (dd, 1H, J = 16.9 Hz, 3.8 Hz), 3.46 (m, 1H), 3.75 (m, 1H), 3.98 (s, 3H), 4.16 (m, 1H), 4.8 (t, 1H, J = 4.2 Hz), 7.35 (m, 9H), 8.16 (d, 1H, J = 9.6 Hz), 11.22 (s, 1H); MS (ESI+): m/z = 513.7, 515.7 [M+H]+ .

As the paragraph descriping shows that 7252-84-8 is playing an increasingly important role.

Reference£º
Patent; VIVALIS; GUEDAT, Philippe; BERECIBAR, Amaya; CIAPETTI, Paola; VENKATA PITHANI, Subhash; TROUCHE, Nathalie; WO2013/171281; (2013); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

Brief introduction of 65202-50-8

65202-50-8 Methyl 6-chloropyridazine-3-carboxylate 12379801, apyridazine compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.65202-50-8,Methyl 6-chloropyridazine-3-carboxylate,as a common compound, the synthetic route is as follows.

EXAMPLE 2The preparation of methyl 3-[3-(5-bromopyrimidin-2-yl)benzyl]-1,2,4-triazolo[4,3-b]pyridazine-6-carboxylate (“A9”) and butyl 3-[3-(5-bromopyrimidin-2-yl)benzyl]-1,2,4-triazolo[4,3-b]pyridazine-6-carboxylate (“A10”), preparation of 3-[3-(5-bromopyrimidin-2-yl)benzyl]-1,2,4-triazolo[4,3-b]-pyridazine-6-carboxylic acid (“A11”), and preparation of N-methyl-3-[3-(5-bromopyrimidin-2-yl)benzyl]-1,2,4-triazolo[4,3-b]pyridazine-6-carboxamide (“A12”) is carried out analogously to the following scheme, 65202-50-8

65202-50-8 Methyl 6-chloropyridazine-3-carboxylate 12379801, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK PATENT GMBH MIT BESCHRAENKTER HAFTUNG; US2011/257173; (2011); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

Downstream synthetic route of 19064-67-6

19064-67-6, 19064-67-6 6-Chloro-3-hydroxypyridazine 252828, apyridazine compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19064-67-6,6-Chloro-3-hydroxypyridazine,as a common compound, the synthetic route is as follows.

General procedure: Method A. A mixture of corresponding chloronitropyridine (Ia-c) (1.59 g, 10 mmol), diazole or 3-chloropyridazin-6-one (10 mmol), and powdered K2CO3 (4.14 g) was thoroughly stirred for several hours at a temperature from 45 to 65 C (the exact time and temperature values are shown for the individual compound). The mixture was then cooled, poured into 100 mL of H2O, and the formed precipitate was filtered off and washed with water.

19064-67-6, 19064-67-6 6-Chloro-3-hydroxypyridazine 252828, apyridazine compound, is more and more widely used in various fields.

Reference£º
Article; Klimenko; Divaeva; Zubenko; Morkovnik; Fetisov; Bodryakov; Russian Journal of Bioorganic Chemistry; vol. 41; 4; (2015); p. 402 – 408; Bioorg. Khim.; vol. 41; 4; (2015); p. 454 – 461,8;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

Downstream synthetic route of 933-76-6

933-76-6 4,5-Dichloro-2-methylpyridazin-3(2H)-one 120462, apyridazine compound, is more and more widely used in various fields.

933-76-6,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.933-76-6,4,5-Dichloro-2-methylpyridazin-3(2H)-one,as a common compound, the synthetic route is as follows.

Step C: Preparation of 4,5-dichloro-6-iodo-2-methyl-3(2H)-pyridazinone (0418) To 4,5-dichloro-2-methyl-3(2H)-pyridazinone (i.e. the product obtained in Example 1, Step B) (5.0 g, 27.9 mmol) dissolved in 80 mL tetrahydrofuran was added 2,2,6,6-bis(tetramethylpiperidine)zinc, magnesium chloride, lithium chloride complex 0.35M in toluene/tetrahydrofuran (i.e. Zn(TMP)2-LiCl-MgCl2 54 mL, 0.35 M in tetrahydrofuran/toluene) 18.75 mmol) over 3 to 5 min. The cloudy reaction mixture was stirred for 15 min and then iodine (8.5 g, 33.51 mmol) was added. The resulting mixture was stirred at ambient temperature for 15 min. The reaction mixture was quenched with aqueous sodium bisulfite solution (to remove excess iodine color), then water (200 mL) followed by 1 N aqueous hydrochloric acid (100 mL). The mixture was extracted with ethyl acetate (300 mL, then 200 mL). The resulting crude product which was purified by silica gel column chromatography eluting with 10% ethyl acetate in petroleum ether. A solid was triturated with diethyl ether and pentane, and the resulting pale yellow solid was dried (3 g). 1H NMR delta 3.83 (s, 3H).

933-76-6 4,5-Dichloro-2-methylpyridazin-3(2H)-one 120462, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; STEVENSON, Thomas Martin; SELBY, Thomas Paul; MARCUS, Kimberly Katherine; (118 pag.)WO2017/74992; (2017); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

 

Analyzing the synthesis route of 1837-55-4

As the paragraph descriping shows that 1837-55-4 is playing an increasingly important role.

1837-55-4, 3,5-Dichloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 95: 5-[(3R)-3-(Methylamino)pyrrolidin-1-yl]-N-(2- methylpropyl)pyridazin-3-arnine. [1 -(delta-Chloro-pyridazin-^yO-pyrrolidin-S-yO-methyl-carbamic acid tert-butyl ester. A solution of 3,5-dichloropyridazine (149 mg, 1.0 mmol) in THF (3 ml_) at 23 0C was treated with (RJ-methyl-pyrrolidin-S-yl-carbamic acid tert-butyl ester (440 mg, 2.2 mmol) and the reaction stirred at 23 0C for 18 h. The reaction diluted with EtOAc (30 ml) and solution washed with water (2 x 5 ml) and combined organic solution dried and concentrated and crude material purified on 16 g SiO2 (O to 30% EtOAc : Hex) to yield 283 mg (91 % yield) of the desired regioisomer and 17 mg (5% yield) of the undesired regioisomer. MS (ESI): mass calcd. for Ci4H2iCIN4O2, 312.5 m/z found, 313.5 [M+H]+. [1 -(delta-lsobutylamino-pyhdazin^-yO-pyrrolidin-S-yO-methyl-carbamic acid tert- butyl ester. A solution of [1-(6-chloro-pyhdazin-4-yl)-pyrrolidin-3-yl]-methyl- carbamic acid tert-butyl ester (32 mg, 0.1 mmol) in isobutylamine (1.0 ml) in a sealed tube was heated to 120 0C for 72 h. The resulting solution was purified directly on 12 g SiO2 (0 to 5% NH3/Me0H:CH2CI2) to yield 20 mg (55% yield). lsobutyl-[5-(3-methylamino-pyrrolidin-1 -yl)-pyhdazin-3-yl]-amine dihydrochlohde. To a stirring solution of [1-(6-isobutylamino-pyhdazin-4-yl)- pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester (19 mg, 0.06 mmol) in 96% formic acid (0.5 ml_) was added 0.05 ml of aqueous 6N HCI. The mixture was stirred for 2 hr, diluted with MeOH and concentrated under reduced pressure (repeat 3X) to give the desired product as a white solid (101 mg, >99%). MS (ESI): mass calcd. for Ci3H23N5, 249.4 m/z found, 250.2 [M+H]. 1H NMR (400 MHz, CD3OD): 8.12 (d, J = 2.5, 1 H), 6.08 (s, 1 H), 4.1 1 – 4.01 (m, 1 H), 4.04 – 3.47 (m, 4H), 3.35 (s, 1 H), 3.15 (d, J = 7.0, 2H), 2.82 (s, 3H), 2.65 – 2.53 (m, 1 H), 2.43 – 2.31 (m, J = 5.6, 1 H), 1.96 (dt, J = 13.4, 6.7, 1 H), 1.03 (d, J = 6.7, 6H)., 1837-55-4

As the paragraph descriping shows that 1837-55-4 is playing an increasingly important role.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; WO2009/152325; (2009); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem