Tag: 1120-95-2

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

The boronate ester (19 g, crude) from Step F above, 3-chloro- pyridazine (4.8 g, 42 mmol), and cesium carbonate (21 g, 63 mmol) were suspended in DMF (120 mL) and water (30 mL). The mixture was purged with argon. 1,1′- Bis(diphenylphosphino)ferrocenedichloropalladium (240 mg, 0.33 mmol) was added to the mixture. The mixture was heated at 1000C for 2 hours. After cooling to room temperature, the reaction mixture was diluted with dichloromethane, and filtered through a pad of Celite. The filtrate was washed with water, brine, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography (98:1.8:0.2 to 95:4.5:0.5 dichloromethane/methanol/concentrated ammonium hydroxide) to give 5-(tert-butyldimethylsilyloxy)-2-methyl-8-(pyridazin-3-yl)-2, 3,4,5- tetrahydro-lH-benzo[c]azepine (4.7 g, 40% for 2 steps) as an oil. This oil was resolved using Chiralcel OD column (eluente :80 etaep:20 IPA:0.1 DEA) to give (+)- enantiomer (2.3 g, 98%, ([alpha]25D, +26.9 (C, 0.29 Methanol) and (-)-enantiomer (2.3 g, 98%, [alpha]25D, -23.2 (C, 0.28 Methanol)): 1H NMR (CDCl3, 300 MHz) delta 9.15 (d, J= 4.8 Hz, IH), 7.91-7.84 (m, 3H), 7.54-7.50 (m, 2H), 4.96 (t, J= 5.2 Hz, IH), 4.26-4.05 (m, IH), 3.85-3.73 (m, IH), 3.30-3.21 (m, IH), 2.97-2.91 (m, IH), 2.32 (s, 3H) 1.95- 1.85 (m, 2H), 0.91 (s, 9H), 0.097-0.085 (m, 6H); ESI MS m/z 370 [M+H]+.The boronate ester (5.5 g, crude) from Step F above, 3-chloro- pyridazine (2.0 g, ~16 mmol), and cesium carbonate (4.2 g, 13 mmol) were suspended in DMF (30 mL) and water (8 mL). The mixture was purged with argon. 1,1′- Bis(diphenylphosphino)ferrocenedichloropalladium (400 mg, 0.52 mmol) was added to the mixture. The mixture was heated at 1000C for 2 hours. After cooling to room temperature, the reaction mixture was diluted with dichloromethane, and filtered through a pad of celite. The filtrate was washed with water, brine, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography (98:1.8:0.2 to 95:4.5:0.5 dichloromethane/methanol/concentrated ammonium hydroxide) to give 5-(tert-butyldimethylsilyloxy)-2-methyl-8-(pyridazin-3-yl)-2, 3,4,5- tetrahydro-lH-benzo[c]azepine (1.3 g, 55% for 2 steps) as an brown oil: 1H NMR (CDCl3, 300 MHz) delta 9.15 (d, J= 4.8 Hz, IH), 7.91-7.84 (m, 3H), 7.54-7.50 (m, 2H), 4.96 (t, J= 5.2 Hz, IH), 4.20-4.10 (m, IH), 3.85-3.73 (m, IH), 2.97-2.91 (m, IH), 2.32 (s, 3H) d, J= 7.9 Hz, IH), 7.24 (d, J= 7.9 Hz, IH ), 4.82 (t, J= 4.9 Hz, IH), 3.64-3.61 (m, IH), 3.27-3.18 (m IH), 2.36 (s, 3H), 1.95-1.85 (m, 2H), 1.80-1.63 (m, 2H), 0.91 (s, 9H), 0.097-0.085 (m, 6H); ESI MS m/z 370 [M+H]+., 1120-95-2

The synthetic route of 1120-95-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; AMR TECHNOLOGY, INC.; BRISTOL-MYERS SQUIBB COMPANY; WO2008/141082; (2008); A1;,
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,1120-95-2

INTERMEDIATE 306,6-Dimethyl-2-[6-(pyrida2in-3-yloxy)-2,3-dihvdro-4H-l,4-benzoxazin-4-yl]-6,7- dihvdro[ 1 ,3]thiazolor5,4-clpyridin-4(5H)-oneA mixture of Intermediate 17 (53 mg, 0.16 mmol), cesium carbonate (105 mg,0.32 mmol) and 3,6-dichloropyridazine (24 mg, 0.16 mmol) in NMP (2 mL) was heated to 1100C for 12 h. After cooling to r.t. it was concentrated in vacuo. Purification by preparative etaPLC (Method 5) gave the title compound (15 mg, 23%) as an off-white solid. deltaeta (CDCl3) 8.94 (IH, dd, J4.5, 1.3 Hz), 8.02 (IH, d, J2.4 Hz), 7.49 (IH, dd, J8.9,4.5 Hz), 7.19 (IH, dd, J 8.9, 1.3 Hz), 6.89-7.03 (2H, m), 5.21 (IH, s), 4.31-4.39 (2H, m),4.09-4.18 (2H, m), 2.86 (2H, s), 1.37 (6H, s).

The synthetic route of 1120-95-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UCB PHARMA S.A.; WO2009/71895; (2009); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1120-95-2,3-Chloropyridazine,as a common compound, the synthetic route is as follows.

(i?)-2-Methyl-l-{3-[4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)- phenoxy]propyl} -pyrrolidine (1.1 g, 3.2 mmol), 3-chloropyridazine (0.485 g, 4.24 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.258 g, 0.223 mmol), K2CO3 (1.19 g, 8.6 mmol) in 1,2-dimethoxyethane (25 mL) and water (11.5 mL) were combined and degassed with argon. The reaction was heated at 85 0C for 15 h, cooled to rt, filtered through celite, taken up in CH2Cl2 (30 mL) and washed with water and saturated NaHCO3 solution. The CH2Cl2 layer was dried (Na2SO4) and evaporated. The product was purified by ISCO chromatography on silica gel, eluting with 5-15% MeOH/ DCM / 0.5% NH4OH. The HCl salt was prepared MeOH – ether-HCl to give a white solid, m.p. 198-201 0C; LCMS m/z = 298 (M + 1).

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Reference£º
Patent; CEPHALON, INC.; WO2009/97306; (2009); A1;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem