1-{1-[5-(Trifluoromethyl)pyridin-2-yl]piperidin-4-yl}methanamine → 4-[5-Cyano-7-(methylthio)-1,3-benzoxazol-2-yl]-N-({1-[5-(trifluoromethyl)pyridin-2-yl]piperidin-4-yl}methyl)benzamide
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:21][CH3:22])[C:6]2[O:10][C:9]([C:11]3[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=3)=[N:8][C:7]=2[CH:20]=1)#[N:2].[F:23][C:24]([F:40])([F:39])[C:25]1[CH:26]=[CH:27][C:28]([N:31]2[CH2:36][CH2:35][CH:34]([CH2:37][NH2:38])[CH2:33][CH2:32]2)=[N:29][CH:30]=1>>[C:1]([C:3]1[CH:4]=[C:5]([S:21][CH3:22])[C:6]2[O:10][C:9]([C:11]3[CH:19]=[CH:18][C:14]([C:15]([NH:38][CH2:37][CH:34]4[CH2:35][CH2:36][N:31]([C:28]5[CH:27]=[CH:26][C:25]([C:24]([F:40])([F:39])[F:23])=[CH:30][N:29]=5)[CH2:32][CH2:33]4)=[O:17])=[CH:13][CH:12]=3)=[N:8][C:7]=2[CH:20]=1)#[N:2]Participants
3
Procedure
The title compound was prepared from 4-[5-cyano-7-(methylthio)-1,3-benzoxazol-2-yl]benzoic acid and 1-{1-[5-(trifluoromethyl)pyridin-2-yl]piperidin-4-yl}methanamine (INTERMEDIATE 5) by a procedure analogous to that described in EXAMPLE 35. Mass spectrum (ESI) 552.0 (M+1). 1H NMR (500 MHz, CDCl3) δ: 8.38 (s, 1H), 8.35 (d, J=8.3 Hz, 2H), 7.94 (d, J=8.3 Hz, 2H), 7.89 (s, 1H), 7.60 (dd, J=2.3 Hz, J=9.2 Hz, 1H), 7.45 (s, 1H), 6.65 (d, J=9.1 Hz, 1H), 6.32 (t, J=5.9 Hz, 1H), 4.46 (d, J=13.3 Hz, 2H), 3.44 (t, J=6.4 Hz, 2H), 2.94 (m, 2H), 2.70 (s, 3H), 1.99 (m, 1H), 1.90 (br d, J=11.6 Hz, 2H), 1.34 (m, 2H).
Sources & evidence
- ORD record
- ord-d313c063a4f4412ea6c98acecc7df1f3
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445480B2
Reaction notes
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