4-Fluoro-3-(trifluoromethoxy)benzoyl chloride → HCID 45141561, compound

HRID 552412Notes

Reaction equation

HRID 552412 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.[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][C:21]=1[O:29][C:30]([F:33])([F:32])[F:31]>>[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([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:25])=[CH:22][C:21]=1[O:29][C:30]([F:31])([F:33])[F:32]

Participants

3

Reactant 2

HCID 177507004-Fluoro-3-(trifluoromethoxy)benzoyl chlorideHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 45141561HCID 45141561, compoundYield 43%

Procedure

Method H was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 4-fluoro-3-(trifluoromethoxy)benzoyl chloride to afford the title compound as a brown solid (25 mg, 43%). 1H-NMR (δ, ppm, DMSO-d6): 6.49 (d, 1H, HPy,5, J=6.0 Hz), 6.93 (d, 1H, Harom, J=8.0 Hz), 7.44 (t, 1H, Harom, J=8.0 Hz), 7.59 (s, 1H, Harom), 7.63 (d, 1H, Harom, J=9.0 Hz), 7.70 (t, 1H, Harom, J=9.0 Hz), 7.81 (d, 1H, HPy,6, J=6.0 Hz), 8-06-8.13 (m, 2H, Harom), 10.47 (s, 1H, NHamide), 11.20 (s, 1H, NHPy3), 11.39 (s, 1H, NHPy2).

Sources & evidence

ORD record
ord-bbb1220b8bd341e8baa4647811323e9f
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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