Tert-butyl 4-bromobenzoate → 4-{4-[4-(3-tert-Butyl-phenylcarbamoyl)-phenyl]-piperidin-1-yl}-benzoic acid tert-butyl ester
Reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12](=[O:25])[C:13]2[CH:18]=[CH:17][C:16]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:26]([O:30][C:31](=[O:39])[C:32]1[CH:37]=[CH:36][C:35](Br)=[CH:34][CH:33]=1)([CH3:29])([CH3:28])[CH3:27].C(C1C=C(NC(C2C=CC(N3CCN(C4C=CC(C(O)=O)=CC=4)CC3)=C(F)C=2)=O)C=CC=1)(C)(C)C>>[C:26]([O:30][C:31](=[O:39])[C:32]1[CH:37]=[CH:36][C:35]([N:22]2[CH2:23][CH2:24][CH:19]([C:16]3[CH:15]=[CH:14][C:13]([C:12](=[O:25])[NH:11][C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=4)=[CH:18][CH:17]=3)[CH2:20][CH2:21]2)=[CH:34][CH:33]=1)([CH3:29])([CH3:27])[CH3:28]Participants
4
Reactant 3
Product 1
Procedure
4-{4-[4-(3-tert-Butyl-phenylcarbamoyl)-phenyl]-piperidin-1-yl}-benzoic acid tert-butyl ester was synthesized from N-(3-tert-butyl-phenyl)-4-piperidin-4-yl-benzamide and 4-bromo-benzoic acid tert-butyl ester in a manner similar to the one described in the synthesis of 4-{4-[4-(3-tert-butyl-phenylcarbamoyl)-2-fluoro-phenyl]-piperazin-1-yl}-benzoic acid above. LCMS calcd for C33H40N2O3 (m/e) 512, obsd 513 (M+H).
Sources & evidence
- ORD record
- ord-dfada6b7a1214a82b9ffc6bea52ed855
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324385B2
Reaction notes
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