Ammonia → 6-Chloro-4-(5-fluoro-6-isopropylpyridin-2-ylamino)pyridazine-3-carboxamide

HRID 1396482Notes

Reaction equation

HRID 1396482 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8](OCC)=[O:9])=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([CH:21]([CH3:23])[CH3:22])[N:15]=2)[CH:3]=1.[NH3:24].CO>>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([NH2:24])=[O:9])=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([CH:21]([CH3:23])[CH3:22])[N:15]=2)[CH:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 86689807Ethyl 6-chloro-4-(5-fluoro-6-isopropylpyridin-2-ylamino)pyridazine-3-carboxylate

Product 1

HCID 866898086-Chloro-4-(5-fluoro-6-isopropylpyridin-2-ylamino)pyridazine-3-carboxamideYield 94%

Conditions

Temperature
40 °C

Procedure

To a solution of ethyl 6-chloro-4-(5-fluoro-6-isopropylpyridin-2-ylamino)pyridazine-3-carboxylate (290 mg, 856 μmol) was added 7N ammonia in MeOH (12.2 mL, 85.6 mmol). The mixture was stirred at 40° C. for 18 h, after which the solvent was removed to give 6-chloro-4-(5-fluoro-6-isopropylpyridin-2-ylamino)pyridazine-3-carboxamide (250 mg, 94%) as an off-white solid. 1H NMR (400 MHz, CHLOROFORM-d6) δ ppm 11.86 (s, 1H), 9.26 (s, 1H), 8.19 (br. s, 1H), 7.36 (t, J=8.8 Hz, 1H), 6.79 (dd, J=8.5, 2.8 Hz, 1H), 5.70 (br. s, 1H), 3.45 (m, 1H), 1.37 (d, J=6.7 Hz, 6H).

Workup

  1. customafter which the solvent was removed

Sources & evidence

ORD record
ord-c18287d1ff024affab89b32b92875c16
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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