2-Chloro-5-cyanobenzoic acid → 2-Chloro-5-cyano-N-(2-(2-(4-fluorophenyl)oxazol-4-yl)-2-methylpropyl)benzamide
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([C:13]([CH3:17])([CH3:16])[CH2:14][NH2:15])[N:12]=2)=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][C:20]=1[C:21](O)=[O:22]>>[Cl:18][C:19]1[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][C:20]=1[C:21]([NH:15][CH2:14][C:13]([C:11]1[N:12]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[O:9][CH:10]=1)([CH3:17])[CH3:16])=[O:22]Participants
3
Procedure
This compound was synthesized from 2-(2-(4-fluorophenyl)oxazol-4-yl)-2-methylpropan-1-amine and 2-chloro-5-cyanobenzoic acid as described in example 8 step 6 (300 mg, yield 44%). 1H NMR (400 MHz, CDCl3) δ 8.02 (d, J=2.0 Hz, 1H), 7.98-7.95 (m, 2H), 7.66-7.63 (m, 1H), 7.56-7.54 (d, J=8.3 Hz, 1H), 7.48 (s, 1H), 7.39 (m, 1H), 7.17-7.13 (t, J=8.8 Hz, 2H), 3.68-3.66 (d, J=5.8 Hz, 2H), 1.41 (s, 6H). MS (ESI) m/z: Calculated for C21H17ClFN3O2: 397.10. found: 396.4 (M−H)−.
Sources & evidence
- ORD record
- ord-a6579794480340c097ecf0c9a64fa15b
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901156B2
Reaction notes
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