2,3,4-Trifluorophenyl isocyanate → 1-(2,3,4-trifluorophenyl)-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.[F:29][C:30]1[C:35]([F:36])=[C:34]([F:37])[CH:33]=[CH:32][C:31]=1[N:38]=[C:39]=[O:40]>>[F:29][C:30]1[C:35]([F:36])=[C:34]([F:37])[CH:33]=[CH:32][C:31]=1[NH:38][C:39]([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:40]Participants
3
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 followed by protection with TBSCl) (0.4 g, 1.0 mmol) was combined with 2,3,4-trifluorophenyl isocyanate (0.32 g, 1.2 mmol) to yield 1-(2,3,4-trifluorophenyl)-3-(3-(2-fluorophenyl)-1-(3-(hydroxymethyl)phenyl)-1H-pyrazol-5-yl)urea (330 mg, 72% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.14 (brs, 1H), 9.01 (s, 1H), 7.98 (dt, J=1.6, and 8.0 Hz, 1H), 7.86 (m, 1H), 7.2-7.6 (m, 8H), 6.96 (d, J=4.0 Hz, 1H), 5.39 (t, J=6.0 Hz, 1H), 4.62 (d, J=6.0 Hz, 2H); MS (EI) m/z: 457.0 (M+H+).
Sources & evidence
- ORD record
- ord-9bdd7360cb0f46ba9a14ee195b66f7fa
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163756B2
Reaction notes
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