2-Fluoro-5-(trifluoromethyl)phenyl isocyanate → 1-(6-fluoro-3-(trifluoromethyl)phenyl)-3-(3-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yloxy)phenyl)urea

HRID 552402Notes

Reaction equation

HRID 552402 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:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=1[N:30]=[C:31]=[O:32]>>[F:19][C:20]1[C:21]([NH: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:22][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 27333802-Fluoro-5-(trifluoromethyl)phenyl isocyanateHCID 451401417-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 451409111-(6-fluoro-3-(trifluoromethyl)phenyl)-3-(3-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yloxy)phenyl)ureaYield 20%

Procedure

Method G was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 2-fluoro-5-trifluoromethyl-phenylisocyanate to afford the title compound (15 mg, 20%). 1H-NMR (DMSO), δ (ppm), J (Hz): 6.45 (d, 1H, HPyr, J=5.9), 6.79 (s, 1H, Harom5′, J=2.1, J=8.0), 7.20 (d, 1H, Harom 4 or 6, J=7.9), 7.21-7.41 (m, 3H, Harom 3′, Harom 2, Harom 6 or 4), 7.50 (t, 1H, Harom 5, J=10.7), 7.79 (d, 1H, HPyr), 8.55 (d, 1H, Harom 4′, J=7.2), 8.93 (s, 1H, NHurea), 9.38 (s, 1H, NHurea), 11.23 (s, 1H, NHim), 11.42 (s, 1H, NHim); MS-LC, Rf=7.64 min, (C20H13F4N5O3), m/z: 448.1 [M++1], 100.

Sources & evidence

ORD record
ord-9dd2f3f7032a47188eb8410604446e59
Source dataset
uspto-grants-2011_05
Patent number
US07951819B2

Reaction notes

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