Ammonia → 6-Chloro-4-(5-chloro-6-methylpyridin-2-ylamino)pyridazine-3-carboxamide
Reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8](OC)=[O:9])=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([CH3:20])[N:14]=2)[CH:3]=1.[NH3:21].CO>>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([NH2:21])=[O:9])=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([CH3:20])[N:14]=2)[CH:3]=1Participants
4
Conditions
- Temperature
- 50 °C
Procedure
A pressure tube was charged with methyl 6-chloro-4-(5-chloro-6-methylpyridin-2-ylamino)pyridazine-3-carboxylate (600 mg, 1.92 mmol) and an ammonia solution in methanol (7M, 20 mL, 140 mmol). The reaction mixture was heated to 50° C. and was stirred for 18 h. The mixture was cooled and concentrated in vacuo to give 6-chloro-4-(5-chloro-6-methylpyridin-2-ylamino)pyridazine-3-carboxamide (665 mg crude, 116%) as a yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) d ppm 11.69 (br. s., 1H), 9.18 (s, 1H), 8.20 (br. s., 1H), 7.61 (d, J=8.59 Hz, 1H), 6.77 (d, J=8.59 Hz, 1H), 5.71 (br. s., 1H), 2.65 (s, 3H). LC-MS 298 [M+H]+. This material was used directly in the next step without further purification.