4-{[({1-[4-(Trifluoromethyl)pyrimidin-2-yl]piperidin-4-yl}methyl)amino]carbonyl}benzoic acid → 4-(7-Bromo-5-cyano-1,3-benzoxazol-2-yl)-N-({1-[4-(trifluoromethyl)pyrimidin-2-yl]piperidin-4-yl}methyl)benzamide

HRID 2093635Notes

Reaction equation

HRID 2093635 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][NH:16][C:17]([C:19]3[CH:27]=[CH:26][C:22]([C:23]([OH:25])=O)=[CH:21][CH:20]=3)=[O:18])[CH2:11][CH2:10]2)[N:4]=1.[Br:30][C:31]1[C:39]2OC(C3C=CC(C([O-])=O)=CC=3)=[N:36][C:35]=2[CH:34]=[C:33]([C:49]#[N:50])[CH:32]=1>>[Br:30][C:31]1[C:39]2[O:25][C:23]([C:22]3[CH:26]=[CH:27][C:19]([C:17]([NH:16][CH2:15][CH:12]4[CH2:13][CH2:14][N:9]([C:5]5[N:4]=[C:3]([C:2]([F:29])([F:1])[F:28])[CH:8]=[CH:7][N:6]=5)[CH2:10][CH2:11]4)=[O:18])=[CH:20][CH:21]=3)=[N:36][C:35]=2[CH:34]=[C:33]([C:49]#[N:50])[CH:32]=1

Participants

3

Reactant 2

HCID 595860784-{[({1-[4-(Trifluoromethyl)pyrimidin-2-yl]piperidin-4-yl}methyl)amino]carbonyl}benzoic acid2×HCID 86643502HCID 86643502, compound2×

Product 1

HCID 687430814-(7-Bromo-5-cyano-1,3-benzoxazol-2-yl)-N-({1-[4-(trifluoromethyl)pyrimidin-2-yl]piperidin-4-yl}methyl)benzamide

Procedure

The title compound was prepared from 4-{[({1-[4-(trifluoromethyl)pyrimidin-2-yl]piperidin-4-yl}methyl)amino]carbonyl}benzoic acid (INTERMEDIATE 25) and 3-amino-5-bromo-4-hydroxybenzonitrile (INTERMEDIATE 1, Step B) by a procedure analogous to that described in Example 109. Mass spectrum (ESI) 587.0 (M+3).

Sources & evidence

ORD record
ord-3f907214f5ed443ca135735e23f27124
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

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