3,4-Difluorophenyl isocyanate → 1-(3,4-Difluorophenyl)-3-(3-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yloxy)phenyl)urea
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:21]=[C:22]([N:27]=[C:28]=[O:29])[CH:23]=[CH:24][C:25]=1[F:26]>>[F:19][C:20]1[CH:21]=[C:22]([NH:27][C:28]([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:29])[CH:23]=[CH:24][C:25]=1[F:26]Participants
3
Procedure
Method G was used with 7-(3-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one and 3,4-difluoro-phenylisocyanate to afford the title compound (16 mg, 23%). 1H-NMR (DMSO), δ (ppm), J (Hz): 6.45 (d, 1H, HPyr, J=5.9), 6.76 (s, 1H, Harom2′, J=2.2, J=11.05), 7.26-7.40 (m, 5H, Harom 6′, Harom 2, Harom 4, Harom 5, Harom 6), 7.56-7.68 (m, 1H, Harom 5′), 7.78 (d, 1H, HPyr), 8.55 (d, 1H, Harom 4′, J=7.2), 9.00 (s, 1H, NHurea), 9.01 (s, 1H, NHurea), 11.17 (s, 1H, NHim), 11.36 (s, 1H, NHim); MS-LC, Rf=7.07 min, (C19H13F2N5O3), m/z: 398.1 [M++1], 100.
Sources & evidence
- ORD record
- ord-c1adb9554b46424683284b4b72ab0e73
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07951819B2
Reaction notes
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