4-Piperazin-1-yl-benzoic acid benzyl ester → 4-{4-[5-(1-Ethyl-1H-indol-6-ylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid benzyl ester
Reaction equation
Cl[C:2]1[CH:21]=[CH:20][C:5]([C:6]([NH:8][C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[CH:14][N:15]3[CH2:18][CH3:19])=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1.[CH2:22]([O:29][C:30](=[O:43])[C:31]1[CH:36]=[CH:35][C:34]([N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)=[CH:33][CH:32]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(OC(=O)C1C=CC(N2CCN(C3C=CC(C(=O)NC4C=CC(C)=C(I)C=4)=CN=3)CC2)=CC=1)C>CCOC(C)=O>[CH2:22]([O:29][C:30](=[O:43])[C:31]1[CH:36]=[CH:35][C:34]([N:37]2[CH2:42][CH2:41][N:40]([C:2]3[CH:21]=[CH:20][C:5]([C:6](=[O:7])[NH:8][C:9]4[CH:17]=[C:16]5[C:12]([CH:13]=[CH:14][N:15]5[CH2:18][CH3:19])=[CH:11][CH:10]=4)=[CH:4][N:3]=3)[CH2:39][CH2:38]2)=[CH:33][CH:32]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
4-{4-[5-(1-Ethyl-1H-indol-6-ylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid benzyl ester was prepared from 6-chloro-N-(1-ethyl-1H-indol-6-yl)-nicotinamide and 4-piperazin-1-yl-benzoic acid benzyl ester following a method similar to the one described in the synthesis of 4-{4-[5-(3-iodo-4-methyl-phenylcarbamoyl)-pyridin-2-yl}-piperazin-1-yl]-benzoic acid ethyl ester above. The product was isolated after silica gel column chromatography with 20-60% EtOAc in hexanes gradient. HRMS m/z calcd for C34H33N5O3 [M+H]+: 560.2656. Found: 560.2656.
Sources & evidence
- ORD record
- ord-8f6966a93e434d52ac0e2e68f273356b
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324385B2
Reaction notes
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