1,3-dimethyl-1H-pyrazol-4-amine → 2-(5-chloro-2-(1,3-dimethyl-1H-pyrazol-4-ylamino)pyridin-4-ylamino)-4-fluoro-N-methylbenzamide

HRID 1045934Notes

Reaction equation

HRID 1045934 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH2:7])[C:4]([CH3:8])=[N:3]1.Cl[C:10]1[CH:15]=[C:14]([NH:16][C:17]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:18]=2[C:19]([NH:21][CH3:22])=[O:20])[C:13]([Cl:28])=[CH:12][N:11]=1>>[Cl:28][C:13]1[C:14]([NH:16][C:17]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:18]=2[C:19]([NH:21][CH3:22])=[O:20])=[CH:15][C:10]([NH:7][C:5]2[C:4]([CH3:8])=[N:3][N:2]([CH3:1])[CH:6]=2)=[N:11][CH:12]=1

Participants

3

Reactant 2

HCID 44310561,3-dimethyl-1H-pyrazol-4-amineHCID 575169242-(2,5-dichloropyridin-4-ylamino)-4-fluoro-N-methylbenzamide

Product 1

HCID 446088822-(5-chloro-2-(1,3-dimethyl-1H-pyrazol-4-ylamino)pyridin-4-ylamino)-4-fluoro-N-methylbenzamide

Procedure

1,3-Dimethylpyrazol-4-amine and 2-(2,5-dichloropyridin-4-ylamino)-4-fluoro-N-methylbenzamide were reacted according to the procedure of example 3.40 to afford 2-(5-chloro-2-(1,3-dimethyl-1H-pyrazol-4-ylamino)pyridin-4-ylamino)-4-fluoro-N-methylbenzamide (23 mg) as a beige solid. 1H NMR spectrum: (300 MHz, DMSO) δ 2.02 (3H, s), 2.71 (3H, d), 3.64 (3H, s), 6.72 (1H, d), 6.86 (1H, td), 7.27 (1H, dd), 7.71 (1H, dd), 7.79 (1H, s), 7.92 (1H, s), 8.04 (1H, s), 8.63 (1H, m), 10.43 (1H, s); Mass spectrum: m/z (ESI+) (M+H)+ =389

Sources & evidence

ORD record
ord-c1392786be8647e09bd51655ca40fa0f
Source dataset
uspto-grants-2013_10
Patent number
US08569298B2

Reaction notes

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