6-Chloro-N-(4-methoxy-2-methyl-phenyl)-nicotinamide → 4-{4-[5-(4-Methoxy-2-methyl-phenylcarbamoyl)-pyridin-2-yl}-piperazin-1-yl]-benzoic acid

HRID 2190605Notes

Reaction equation

HRID 2190605 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:41]=[CH:40][C:27]([C:28]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][C:32]=2[CH3:39])=[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>>[CH3:38][O:37][C:34]1[CH:35]=[CH:36][C:31]([NH:30][C:28]([C:27]2[CH:40]=[CH:41][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])=[C:32]([CH3:39])[CH:33]=1

Participants

4

Reactant 3

HCID 98568436-Chloro-N-(4-methoxy-2-methyl-phenyl)-nicotinamideHCID 539216634-Piperazin-1-yl-benzoic acid benzyl esterHCID 593179834-[4-(5-Phenylcarbamoyl-pyridin-2-yl)-piperazin-1-yl]-benzoic acid

Product 1

HCID 593181814-{4-[5-(4-Methoxy-2-methyl-phenylcarbamoyl)-pyridin-2-yl}-piperazin-1-yl]-benzoic acid

Procedure

4-{4-[5-(4-Methoxy-2-methyl-phenylcarbamoyl)-pyridin-2-yl}-piperazin-1-yl]-benzoic acid was prepared from 4-piperazin-1-yl-benzoic acid benzyl ester and 6-chloro-N-(4-methoxy-2-methyl-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 C25H26N4O4 [M+H]+: 447.2027. Found: 447.2027.

Sources & evidence

ORD record
ord-0e4082ab80534959bfcd5da7febba4c4
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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