1-benzyl-3-tert-butyl-1H-pyrazole-5-carbonyl chloride → HCID 45142431, compound

HRID 552418Notes

Reaction equation

HRID 552418 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.[CH2:19]([N:26]1[C:30]([C:31](Cl)=[O:32])=[CH:29][C:28]([C:34]([CH3:37])([CH3:36])[CH3:35])=[N:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:19]([N:26]1[C:30]([C:31]([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:32])=[CH:29][C:28]([C:34]([CH3:37])([CH3:36])[CH3:35])=[N:27]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 27993221-benzyl-3-tert-butyl-1H-pyrazole-5-carbonyl chlorideHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 45142431HCID 45142431, compoundYield 39%

Procedure

Method H was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 1-benzyl-3-tert-butyl-1H-pyrazole-5-carbonyl chloride to afford the title compound (40 mg, 39%). 1H-NMR (δ, ppm, DMSO-d6): 1.29 (s, 9H, t-Bu), 5.67 (s, 2H, CH2), 6.47 (d, 1H, HPy,5, J=6.0 Hz), 6.89 (d, 1H, Harom, J=8.0 Hz), 7.00 (s, 1H, Hpyrrazole), 7.11 (d, 2H, Harom, J=8.0 Hz), 7.22 (t, 1H, Harom, J=7.0 Hz), 7.11 (t, 2H, Harom, J=8.0 Hz), 7.40 (t, 1H, Harom, J=8.0 Hz), 7.48-7.51 (m, 1H, Harom), 7.60 (d, 1H, Harom, J=8.0 Hz), 7.79 (d, 1H, HPy,6, J=6.0 Hz), 10.23 (s, 1H, NHamide), 11.18 (s, 1H, NHPy3), 11.38 (s, 1H, NHPy2). HRMS (EI): m/z [M+H] calcd for C27H27N6O3: 483.2145; found: 483.2145.

Sources & evidence

ORD record
ord-b94891cb690e44799f97815e9103e243
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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