2,5-Dimethyl-2H-pyrazole-3-carbonyl chloride → HCID 45142203, compound

HRID 552415Notes

Reaction equation

HRID 552415 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.[CH3:19][N:20]1[C:24]([C:25](Cl)=[O:26])=[CH:23][C:22]([CH3:28])=[N:21]1>>[CH3:19][N:20]1[C:24]([C:25]([NH:1][C:2]2[CH:18]=[CH:17][CH:16]=[C:4]([O:5][C:6]3[CH:11]=[CH:10][N:9]=[C:8]4[NH:12][C:13](=[O:15])[NH:14][C:7]=34)[CH:3]=2)=[O:26])=[CH:23][C:22]([CH3:28])=[N:21]1

Participants

3

Reactant 2

HCID 27362992,5-Dimethyl-2H-pyrazole-3-carbonyl chlorideHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 45142203HCID 45142203, compoundYield 26%

Procedure

Method H was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 1,3-dimethyl-1H-pyrazole-5-carbonyl chloride to afford the title compound (20 mg, 26%). 1H-NMR (δ, ppm, DMSO-d6): 2.19 (s, 3H, Mepyrrazole,3), 3.98 (s, 3H, Mepyrrazole,1), 6.48 (d, 1H, HPy,5, J=6.0 Hz), 6.81 (s, 1H, Hpyrrazole), 6.91 (d, 1H, Harom, J=8.0 Hz), 7.41 (t, 1H, Harom, J=8.0 Hz), 7.56 (s, 1H, Harom), 7.61 (d, 1H, Harom, J=8.0 Hz), 7.80 (d, 1H, HPy,6, J=6.0 Hz), 10.19 (s, 1H, NHamide), 11.19 (s, 1H, NHPy3), 11.39 (s, 1H, NHPy2). HRMS (EI): m/z [M+H] calcd for C18H17N6O3: 365.1362; found: 365.1356.

Sources & evidence

ORD record
ord-4116b743cadf4ef188fe8617f8f6bdb3
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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