1-phenyl-5-(trifluoromethyl)pyrazole-4-carbonyl chloride → HCID 45142432, compound

HRID 552417Notes

Reaction equation

HRID 552417 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[NH:12][C:13](=[O:15])[NH:14][C:7]=12.[C:19]1([N:25]2[C:29]([C:30]([F:33])([F:32])[F:31])=[C:28]([C:34](Cl)=[O:35])[CH:27]=[N:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[O:15]=[C:13]1[NH:12][C:8]2=[N:9][CH:10]=[CH:11][C:6]([O:5][C:4]3[CH:3]=[C:2]([NH:1][C:34]([C:28]4[CH:27]=[N:26][N:25]([C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=5)[C:29]=4[C:30]([F:32])([F:33])[F:31])=[O:35])[CH:18]=[CH:17][CH:16]=3)=[C:7]2[NH:14]1

Participants

3

Reactant 2

HCID 27764451-phenyl-5-(trifluoromethyl)pyrazole-4-carbonyl chlorideHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 45142432HCID 45142432, compoundYield 28%

Procedure

Method H was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carbonyl chloride to afford the title compound (28 mg, 28%). 1H-NMR (δ, ppm, DMSO-d6): 6.50 (d, 1H, HPy,5, J=6.0 Hz), 6.92 (d, 1H, Harom, J=8.0 Hz), 7.43 (t, 1H, Harom, J=8.0 Hz), 7.51-7.63 (m, 7H, Harom), 7.81 (d, 1H, HPy,6, J=6.0 Hz), 8.29 (s, 1H, Hpyrrazole), 10.63 (s, 1H, NHamide), 11.19 (s, 1H, NHPy3), 11.39 (s, 1H, NHPy2). HRMS (EI): m/z [M+H] calcd for C23H16N6O3F3: 481.1236; found: 481.1229.

Sources & evidence

ORD record
ord-58bf1c6f0df1436db9305f9d60925f7d
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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