1-Phenyl-1H-pyrazole-5-carbonyl chloride → HCID 45142204, compound

HRID 552416Notes

Reaction equation

HRID 552416 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](Cl)=[O:31])=[CH:28][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:30]([C:29]4[N:25]([C:19]5[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:26]=[CH:27][CH:28]=4)=[O:31])[CH:18]=[CH:17][CH:16]=3)=[C:7]2[NH:14]1

Participants

3

Reactant 2

HCID 27765651-Phenyl-1H-pyrazole-5-carbonyl chlorideHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 45142204HCID 45142204, compoundYield 17%

Procedure

Method H was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 1-phenyl-1H-pyrazole-5-carbonyl chloride to afford the title compound (15 mg, 17%). 1H-NMR (δ, ppm, DMSO-d6): 6.47 (d, 1H, HPy,5, J=6.0 Hz), 6.89 (d, 1H, Harom, J=8.0 Hz), 7.06 (d, 1H, Hpyrrazole, J=2.1 Hz), 7.37-7.49 (m, 7H, Harom), 7.53 (d, 1H, Harom, J=8.0 Hz), 7.78-7.81 (m, 2H, Hpyrrazole+Py,6), 10.64 (s, 1H, NHamide), 11.16 (s, 1H, NHPy3), 11.37 (s, 1H, NHPy2). HRMS (EI): m/z [M+H] calcd for C22H17N6O3: 413.1362; found: 413.1366.

Sources & evidence

ORD record
ord-8a85618aca524b5d8f2aebf1e00b951e
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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