Ammonia → 6-Chloro-4-(5,6-dimethylpyridin-2-ylamino)pyridazine-3-carboxamide

HRID 1396381Notes

Reaction equation

HRID 1396381 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]([CH3:20])=[C:16]([CH3:21])[N:15]=2)[CH:3]=1.CO.[NH3:24]>>[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]([CH3:20])=[C:16]([CH3:21])[N:15]=2)[CH:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 86689719Ethyl 6-chloro-4-(5,6-dimethylpyridin-2-ylamino)pyridazine-3-carboxylate

Product 1

HCID 866897206-Chloro-4-(5,6-dimethylpyridin-2-ylamino)pyridazine-3-carboxamideYield 100%

Procedure

In a 50 mL round bottom flask, ethyl 6-chloro-4-(5,6-dimethylpyridin-2-ylamino)pyridazine-3-carboxylate (929 mg, 3.03 mmol) was suspended in ammonia 7M in methanol (7.87 g, 10.0 mL, 70.0 mmol). The flask was sealed and stirred for 2 h at room temperature. Solvents evaporated and solid residue dried in high vacuum to give 6-chloro-4-(5,6-dimethylpyridin-2-ylamino)pyridazine-3-carboxamide (841 mg, 100% yield) as an off-white solid. 1H NMR (CHLOROFORM-d) δ: 11.37 (br. s., 1H), 9.11 (s, 1H), 8.09 (br. s., 1H), 7.32 (d, J=8.3 Hz, 1H), 6.63 (d, J=8.1 Hz, 1H), 5.59 (br. s., 1H), 2.43 (s, 3H), 2.19 (s, 3H); LC-MS 278.0 [M+H]+.

Workup

  1. customThe flask was sealed
  2. customSolvents evaporated
  3. customsolid residue dried in high vacuum

Sources & evidence

ORD record
ord-762937d30dad4fe0bf3144b76ffdc675
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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