4-{[({1-[4-(Trifluoromethyl)pyrimidin-2-yl]piperidin-4-yl}methyl)amino]carbonyl}benzoic acid → 4-[5-Cyano-7-(trifluoromethoxy)-1,3-benzoxazol-2-yl]-N-({1-[4-(trifluoromethyl)pyrimidin-2-yl]piperidin-4-yl}methyl)benzamide
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11][C:12]([F:15])([F:14])[F:13])[C:9]=1[OH:10])[C:5]#[N:6].[F:16][C:17]([F:44])([F:43])[C:18]1[CH:23]=[CH:22][N:21]=[C:20]([N:24]2[CH2:29][CH2:28][CH:27]([CH2:30][NH:31][C:32]([C:34]3[CH:42]=[CH:41][C:37]([C:38](O)=O)=[CH:36][CH:35]=3)=[O:33])[CH2:26][CH2:25]2)[N:19]=1>>[C:5]([C:4]1[CH:7]=[C:8]([O:11][C:12]([F:13])([F:14])[F:15])[C:9]2[O:10][C:38]([C:37]3[CH:36]=[CH:35][C:34]([C:32]([NH:31][CH2:30][CH:27]4[CH2:28][CH2:29][N:24]([C:20]5[N:19]=[C:18]([C:17]([F:43])([F:44])[F:16])[CH:23]=[CH:22][N:21]=5)[CH2:25][CH2:26]4)=[O:33])=[CH:42][CH:41]=3)=[N:1][C:2]=2[CH:3]=1)#[N:6]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared from 3-amino-4-hydroxy-5-(trifluoromethoxy)benzonitrile and 4-{[({1-[4-(trifluoromethyl)pyrimidin-2-yl]piperidin-4-yl}methyl)amino]carbonyl}benzoic acid (INTERMEDIATE 25) by a procedure analogous to that described in EXAMPLE 109. Mass spectrum (ESI) 591.1 (M+1). 1H NMR (500 MHz, CDCl3) δ: 8.47 (d, J=4.8 Hz, 1H), 8.36 (d, J=8.2 Hz, 2H), 8.06 (s, 1H), 7.97 (d, J=8.2 Hz, 2H), 7.59 (s, 1H), 6.72 (d, J=4.6 Hz, 1H), 6.33 (t, J=5.9 Hz, 1H), 4.87 (d, J=13.5 Hz, 2H), 3.45 (t, J=6.4 Hz, 2H), 2.93 (m, 2H), 2.00 (m, 1H), 1.90 (br d, J=11.6 Hz, 2H), 1.31 (m, 2H).
Sources & evidence
- ORD record
- ord-18f6e67c473c4d5a88068f29b4a568d0
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445480B2
Reaction notes
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