1,2-Dichloro-3-isocyanatobenzene → 1-(2,3-dichlorophenyl)-3-(3-(2-fluorophenyl)-1-(3-(hydroxymethyl)phenyl)-1H-pyrazol-5-yl)urea
Reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([N:16]2[C:20]([NH2:21])=[CH:19][C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])=[N:17]2)[CH:13]=[CH:14][CH:15]=1)(C(C)(C)C)(C)C.[Cl:29][C:30]1[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=1[N:37]=[C:38]=[O:39]>>[Cl:29][C:30]1[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=1[NH:37][C:38]([NH:21][C:20]1[N:16]([C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([CH2:9][OH:8])[CH:11]=2)[N:17]=[C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[F:28])[CH:19]=1)=[O:39]Participants
Procedure
Using general method A, 1-(3-((t-butyldimethylsilyloxy)methyl)phenyl)-3-(2-fluorophenyl)-1H-pyrazol-5-amine (available from ethyl 3-(5-amino-3-(2-fluorophenyl)-1H-pyrazol-1-yl)benzoate using general method C, followed by protection with TBSCl) (0.4 g, 1.0 mmol) was combined with 2,3-dichlorophenyl isocyanate (0.32 g, 1.2 mmol) to yield 1-(2,3-dichlorophenyl)-3-(3-(2-fluorophenyl)-1-(3-(hydroxymethyl)phenyl)-1H-pyrazol-5-yl)urea (0.28 g, 59% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.05 (s, 1H), 8.87 (s, 1H), 8.08 (m, 1H), 7.99 (dt, J=2.0, and 8.0 Hz, 1H), 7.58 (m, 1H), 7.55 (d, J=7.6 Hz, 1H), 7.50 (brd, J=7.6 Hz, 1H), 7.45 (brd, J=7.2 Hz, 1H), 7.41 (m, 1H), 7.32 (m, 3H), 6.91 (d, J=4.4 Hz, 1H), 5.39 (t, J=6.0 Hz, 1H), 4.62 (d, J=6.0 Hz, 2H); MS (EI) m/z: 471.0 (M+H+).
Sources & evidence
- ORD record
- ord-74f162d0ccda47128a80e6af51b1824f
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163756B2
Reaction notes
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