4-Piperazin-1-yl-benzoic acid benzyl ester → 4-{4-[5-(2-Fluoro-4-trifluoromethyl-phenylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid
Reaction equation
C([O:8][C:9](=[O:22])[C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:12][CH:11]=1)C1C=CC=CC=1.Cl[C:24]1[CH:43]=[CH:42][C:27]([C:28]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][C:32]=2[F:41])=[O:29])=[CH:26][N:25]=1.C1(NC(C2C=CC(N3CCN(C4C=CC(C(O)=O)=CC=4)CC3)=NC=2)=O)C=CC=CC=1>>[F:41][C:32]1[CH:33]=[C:34]([C:37]([F:40])([F:39])[F:38])[CH:35]=[CH:36][C:31]=1[NH:30][C:28]([C:27]1[CH:42]=[CH:43][C:24]([N:19]2[CH2:18][CH2:17][N:16]([C:13]3[CH:12]=[CH:11][C:10]([C:9]([OH:8])=[O:22])=[CH:15][CH:14]=3)[CH2:21][CH2:20]2)=[N:25][CH:26]=1)=[O:29]Participants
4
Reactant 3
Product 1
Procedure
4-{4-[5-(2-Fluoro-4-trifluoromethyl-phenylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid was prepared from 4-piperazin-1-yl-benzoic acid benzyl ester and 6-chloro-N-(2-fluoro-4-trifluoromethyl-phenyl)-nicotinamide with a method similar to the one described in the synthesis of 4-[4-(5-phenylcarbamoyl-pyridin-2-yl)-piperazin-1-yl]-benzoic acid above. HRMS m/z calcd for C24H20N4O3F4 [M+H]+: 489.1545. Found: 489.1543.
Sources & evidence
- ORD record
- ord-3063218005f948428ed11ac3088fb101
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324385B2
Reaction notes
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