Ammonia → 6-chloro-4-(1-methyl-1H-pyrazol-3-ylamino)-pyridazine-3-carboxylic acid amide

HRID 1396353Notes

Reaction equation

HRID 1396353 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[N:7][C:8]([Cl:18])=[CH:9][C:10]=1[NH:11][C:12]1[CH:16]=[CH:15][N:14]([CH3:17])[N:13]=1)=O.[NH3:19]>CO>[Cl:18][C:8]1[N:7]=[N:6][C:5]([C:3]([NH2:19])=[O:2])=[C:10]([NH:11][C:12]2[CH:16]=[CH:15][N:14]([CH3:17])[N:13]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86689721HCID 86689721, compound

Product 1

HCID 866897226-chloro-4-(1-methyl-1H-pyrazol-3-ylamino)-pyridazine-3-carboxylic acid amideYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Chloro-4-(1-methyl-1H-pyrazol-3-ylamino)-pyridazine-3-carboxylic acid methyl ester (75 mg, 0.28 mmol) was suspended in 7M ammonia in methanol (3 mL). After 16 h, the reaction mixture was concentrated in vacuo to give 6-chloro-4-(1-methyl-1H-pyrazol-3-ylamino)-pyridazine-3-carboxylic acid amide (70 mg, 100%) as an off-white solid which was used directly in the next step without purification. 1H NMR (300 MHz, DMSO-d6) δ ppm 11.39 (s, 1H) 8.77 (br. s., 1H) 8.24 (s, 1H) 8.13 (br. s., 1H) 7.72 (d, J=2.3 Hz, 1H) 6.18 (d, J=2.3 Hz, 1H) 3.84 (s, 3H); LCMS (EI/CI) m/z: 253 [M+H].

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-5bf733292c25497e90b2ebb81508d5bc
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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