6-chloro-N-(3,5-dimethoxyphenyl)pyridine-3-carboxamide → 4-{4-[5-(3,5-Dimethoxy-phenylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid

HRID 2190606Notes

Reaction equation

HRID 2190606 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:42]=[CH:41][C:27]([C:28]([NH:30][C:31]2[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[C:33]([O:39][CH3:40])[CH:32]=2)=[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>>[CH3:40][O:39][C:33]1[CH:32]=[C:31]([NH:30][C:28]([C:27]2[CH:41]=[CH:42][C:24]([N:19]3[CH2:18][CH2:17][N:16]([C:13]4[CH:12]=[CH:11][C:10]([C:9]([OH:8])=[O:22])=[CH:15][CH:14]=4)[CH2:21][CH2:20]3)=[N:25][CH:26]=2)=[O:29])[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=1

Participants

4

Reactant 3

HCID 21016456-chloro-N-(3,5-dimethoxyphenyl)pyridine-3-carboxamideHCID 539216634-Piperazin-1-yl-benzoic acid benzyl esterHCID 593179834-[4-(5-Phenylcarbamoyl-pyridin-2-yl)-piperazin-1-yl]-benzoic acid

Product 1

HCID 593179984-{4-[5-(3,5-Dimethoxy-phenylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid

Procedure

4-{4-[5-(3,5-Dimethoxy-phenylcarbamoyl)-pyridin-2-yl]-piperazin-1-yl}-benzoic acid was prepared from 4-piperazin-1-yl-benzoic acid benzyl ester and 6-chloro-N-(3,5-dimethoxy-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 C25H26N4O5 [M+H]+: 463.1976. Found: 463.1977

Sources & evidence

ORD record
ord-e65d7cdd177e47198bd611fb6e413b4e
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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