Heterocyclic Building Blocks-Pyridazine

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.

933-76-6, Step 1: 4-bromo-5-chloro-2-methy]pyridazin-3(2H)-one 4,5-dichloro-2-methylpyridazin-3(2H)-one (180 mg, 1.01 mmol) was dissolved in 48% aqueous HBr (5 mL, 45 mmol). The reaction mixture was heated at 100 C for 16 hours. The reaction mixture was cooled down and basified up to pH = 8 with 1M aq. NaOH. The mixture was extracted with EtOAc. The organic layer was washed with brine, dried with Na2S04, filtered and evaporated under reduced pressure to afford a mixture of 4-bromo-5-chloro-2-methylpyridazin- 3(2H)-one and 5-bromo-4-chloro-2-methylpyridazin-3(2H)-one (280 mg, 1.253 mmol) in quantitative yield. LCMS (ESI+): 223 / 225 / 227 (M+H , Br, CI pattern). Step 2: 4-brorao-2-methyl-5-((l-methylazepan-3-yI)amiao)pyridaziii-3(2H)- The 4-bromo-5-chloro-2-methylpyridazin-3(2H)-one and 5-bromo-4-chloro-2-methylpyridazin- 3(2H)-one (280 mg, 1.253 mmol), l-methylazepan-3 -amine (0.209 g, 1.63 mmol), N-ethyl-N- isopropylpropan-2-amine (0.243 g, 1.88 mmol) and n-BuOH (1.5 mL) were charged in a microwave vial. The reaction was heated to 160 C for 60 min. The mixture of regioisomers was purified by flash chromatography (10% to 100% of 1 : 10:90 NH4OH:MeOH:DCM in DCM eluent gradient) to afford two sets of fractions. The later eluting fractions (most polar compound) were combined and evaporated under reduced pressure to afford 4-bromo-2-methyl- 5-((l -methylazepan-3-yl)amino)pyridazin-3(2H)-one (155 mg, 0.395 mmol) in 39% yield. lH NMR (400MHz, DMSO-d6) delta 7.77 (s, 1H), 6.20 (d, J= 8.8 Hz, 1H), 3.96 (br. s, 1 H), 3.57 (s, 3H), 2.55-2.75 (m, 3H), 2.34-2.45 (m, 1H), 2.37 (s, 3H), 1.31-1.74 (m, 6H). LCMS (ESI+): 315 / 317 (M+H, Br pattern).

The synthetic route of 933-76-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; BURDICK, Daniel, J.; COTE, Alexandre; DUPLESSIS, Martin; NASVESCHUK, Christopher, G.; TAYLOR, Alexander, M.; (117 pag.)WO2016/112298; (2016); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

50681-25-9, 4-Pyridazinecarboxylic Acid is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

50681-25-9, EXAMPLE 11 [1S-(1R*,2S*,3S*)]-N-[4-[(Butylamino)sulfonyl]-1-(cyclohexylmethyl)-2,3-dihydroxybutyl]-4-pyridazinecarboxamide Following the procedure of Example 6 but employing molar equivalent amounts of 4-pyridazine carboxylic acid (33 mg., 0.268 mmole, 1 eq.) and the product of Example 1 (100 mg., 0.268 mmole, 1 eq.), 31 mg. of white solid [1S-(1R*,2S*,3S*)]-N-[4-[(butylamino)sulfonyl]-1-(cyclohexylmethyl)-2,3-dihydroxybutyl]-4-pyridazinecarboxamide were obtained; m.p. 170-172; [alpha]D =-29.1 (c=0.43, methanol). TLC (silica gel; 10% methanol in dichloromethane containing 0.2% NH4 OH) Rf =0.46.

As the paragraph descriping shows that 50681-25-9 is playing an increasingly important role.

Reference£º
Patent; E. R. Squibb & Sons, Inc.; US5098924; (1992); A;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2166-31-6,6-Phenylpyridazin-3(2H)-one,as a common compound, the synthetic route is as follows.

135 ml (135 mmole) of a solution of phenylmagnesium bromide (IM) in THF was added to a hot suspension of 6-phenylpyridazinone compound 7.8g (45 mmole) in dry toluene (50 ml). The mixture was refluxed for 8h, left overnight at ambient temperature, then decomposed with a saturated solution of ammonium chloride. The organic layer was separated, and the aqueous layer was extracted with 100ml of ethyl acetate. The solvent was removed and the residue was crystallized from ethanol. The crystals were collected by filtering and dried over a medium frit sintered glass funnel in vacuo to give 5.6 g of white crystals. Yield was 50%, confirmed by ESI-MS. ESI-MS: m/z 250.1 (M+H+).

2166-31-6, As the paragraph descriping shows that 2166-31-6 is playing an increasingly important role.

Reference£º
Patent; NORTHWESTERN UNIVERSITY; WO2007/127474; (2007); A2;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

1120-95-2, 3-Chloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 3-chloropyridazine (1 g, 8.73 mmol), tert-butyl piperazine-1-carboxylate(1.626 g, 8.73 mmol), and K2C03 (2.413 g, 17.46 mmol) in NMP (10 mL) was stirred at 120 C for 16 h. The mixture was purified by chromatography (silica, EtOAc/PE =1/20) to afford tertbutyl 4-(pyridazin-3-yl)piperazine-1-carboxylate (709 mg, 2.68 mmol, 31%) as a yellow oil. ESIMS (EI+, m/z): 265.4 [M+H]t

1120-95-2, Big data shows that 1120-95-2 is playing an increasingly important role.

Reference£º
Patent; NAVITOR PHARMACEUTICALS, INC.; O’NEILL, David John; SAIAH, Eddine; KANG, Seong Woo Anthony; BREARLEY, Andrew; BENTLEY, Jonathan; (565 pag.)WO2018/89433; (2018); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

932-22-9, 4,5-Dichloro-3(2H)-pyridazinone is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,932-22-9

4,5-dichloro-2-methyl-pyridazin-3-one To a stirred solution of 4,5-dichloro-1H-pyridazin-6-one (25.0 g, 152 mmol) in N,N-dimethylformamide (152 ml) was added potassium carbonate (25.4 g, 182 mmol) and iodomethane (25.8 g, 182 mmol, 11.3 ml). The resulting mixture was stirred at room temperature overnight. The reaction mixture was then poured onto ice-water (300 ml) and the mixture stirred for 15 mins. The resulting precipitate was collected by filtration, then dissolved in dichloromethane and passed through a phase separation cartridge. The organics were concentrated in vacuo to give 19.7 g of a pale brown solid. 1H NMR (400 MHz, Chloroform) d ppm 3.83 (s, 3H) 7.77 (s, 1H)

The synthetic route of 932-22-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SYNGENTA LIMITED; Bhonoah, Yunas; Elliott, Alison Clare; Gaulier, Steven; Ling, Kenneth; Mitchell, Glynn; Morris, James Alan; Rzepa, Paula Rocha; Viner, Russell Colin; US2014/256546; (2014); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

1445-56-3, 3-Chloropyridazine-4-carbonitrile is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A soln. of halide BB-5 (1 eq) and amine BB-6 (2.2 eq) in anh. EtOH was heated to 70C and stirred for 24h at RT (see Table 27). The volatiles were evaporated and the residue was partitioned between a 10% aq. soln. of Na2CC>3 and EtOAc. The aq. phase was extracted with EtOAc (2x) and the combined org. phases were washed with brine, dried over MgSCh and concentrated in vacuo. The crude was purified by CC using Hept/EtOAc., 1445-56-3

As the paragraph descriping shows that 1445-56-3 is playing an increasingly important role.

Reference£º
Patent; IDORSIA PHARMACEUTICALS LTD; FROIDEVAUX, Sylvie; HUBLER, Francis; MURPHY, Mark; RENNEBERG, Dorte; STAMM, Simon; (97 pag.)WO2019/141808; (2019); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

141-30-0, 3,6-Dichloropyridazine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 2. 6-4-f4- (5-Chloro-lH-indole-2-sulphonyl)-piperazine-l-carbonvl]-phenyl}-2- (2-dimethylamino-ethvl)-2H-pyridazin-3-one Step A. To a microwave vial was added 3,6-dichloropyridazine (645mg, 4.33mmol), potassium acetate (425 mg, 4.33 mmol) and 9 mL acetic acid/water (5: 1). The reaction mixture was heated at 140 C for 70 minutes. The solvent was evaporated and the crude was purified by preparative HPLC using a gradient of acetonitrile/5 % acetonitrile- water phase containing 0.1 M ammonium acetate, to give 436 mg of 6-chloro-2H- pyridazin-3-one (77 % yield). 1H NMR (400 MHz ; methanol-d4 as solvent and internal reference) delta (ppm) 6.96 (d, 1H), 7.45 (d, 1H)., 141-30-0

141-30-0 3,6-Dichloropyridazine 67331, apyridazine compound, is more and more widely used in various fields.

Reference£º
Patent; ASTRAZENECA AB; WO2005/65688; (2005); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

89180-50-7, 5,6-Dichloropyridazin-4-amine is a pyridazine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,89180-50-7

5,6-dichloropyridazine-4-amine (4.01 g, 24.5 mmol)And hydrazine (80%[w/w]Aqueous solution, 26.20g, 419mmol)The mixture was stirred at 90 C for 3 hours.Then cool to room temperature,Add water (20mL),Then a yellow solid precipitates,The filtered cake was collected as a yellow solid (3.51 g, yield 90%).

As the paragraph descriping shows that 89180-50-7 is playing an increasingly important role.

Reference£º
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Li Minxiong; Peng Ju; Li Xiaobo; Zhang Tao; Hu Haiyang; Chen Wuhong; Bai Changlin; Ke Donghua; Chen Peng; (217 pag.)CN109776522; (2019); A;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1228788-25-7,Pyridazin-3-ylmethanamine hydrochloride,as a common compound, the synthetic route is as follows.

To a solution of 2,3,6-trifluorophenyl acetic acid (5.5 g, 29 mmol) and the intermediate from Step C (5.0 g, 34 mmol) in DCM (20 mL) was added EDC (7.9 g, 41.2 mmol) followed by DIEA (17.99 mL, 103 mmol). After stirring the reaction at room temperature for 18 hours, it was diluted with DCM (100 mL), and washed with water (2X). The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to give a brown solid. LC3 rt = 0.6 min, m/z = 282 (M+H)., 1228788-25-7

1228788-25-7 Pyridazin-3-ylmethanamine hydrochloride 53419881, apyridazine compound, is more and more widely used in various fields.

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

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.

Compound 2 (2 mmol),4-methoxycarbonylbenzeneboronic acid (2 mmol),Copper acetate (0.4 mmol),Pyridine (0.4 mmol) in the reaction flask,Add 15 mL of DMF and dissolve at room temperature with stirring.Open reaction for about 4 hours,The reaction was complete by TLC.Add appropriate amount of ethyl acetate for extraction.Washed with saturated saline,The organic phase is concentrated,Separation and purification by silica gel column chromatography (ethyl acetate /Petroleum ether = 1/3),Obtained 2.1 g of white solid compound 25,The yield was 80%.

19064-67-6, The synthetic route of 19064-67-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Hu Youhong; Geng Meiyu; Duan Wenwen; Ding Jian; Wan Penghui; Shen Aijun; Lu Dong; Liu Hongchun; Wei Aihuan; Zhang Minmin; Zeng Limin; Cao Jingchen; (57 pag.)CN109280032; (2019); A;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem