6-[4-(4-Methoxy-benzyl)-piperazin-1-ylmethyl]-pyridin-3-ylamine → 5-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid {6-[4-(4-methoxy-benzyl)-piperazin-1-ylmethyl]-pyridin-3-yl}-amide

HRID 43204Notes

Reaction equation

HRID 43204 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[CH:22]=[CH:21][C:20]([C:23](O)=[O:24])=[C:19]2[C:14]=1[CH:15]=[CH:16][CH:17]=[N:18]2.[CH3:26][O:27][C:28]1[CH:48]=[CH:47][C:31]([CH2:32][N:33]2[CH2:38][CH2:37][N:36]([CH2:39][C:40]3[N:45]=[CH:44][C:43]([NH2:46])=[CH:42][CH:41]=3)[CH2:35][CH2:34]2)=[CH:30][CH:29]=1>C(Cl)Cl.CO>[CH3:26][O:27][C:28]1[CH:29]=[CH:30][C:31]([CH2:32][N:33]2[CH2:38][CH2:37][N:36]([CH2:39][C:40]3[N:45]=[CH:44][C:43]([NH:46][C:23]([C:20]4[CH:21]=[CH:22][C:13]([C:3]5[C:4]([Cl:12])=[C:5]([O:10][CH3:11])[CH:6]=[C:7]([O:8][CH3:9])[C:2]=5[Cl:1])=[C:14]5[C:19]=4[N:18]=[CH:17][CH:16]=[CH:15]5)=[O:24])=[CH:42][CH:41]=3)[CH2:35][CH2:34]2)=[CH:47][CH:48]=1

Participants

4

Reactant 2

HCID 592928516-[4-(4-Methoxy-benzyl)-piperazin-1-ylmethyl]-pyridin-3-ylamineHCID 592929115-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid

Product 1

HCID 592928915-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid {6-[4-(4-methoxy-benzyl)-piperazin-1-ylmethyl]-pyridin-3-yl}-amide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared in analogy to the procedure described in Step 14.1 but using 5-(2,6-dichloro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid (Step 159.1), 6-[4-(4-methoxy-benzyl)-piperazin-1-ylmethyl]-pyridin-3-ylamine (Step 111.1) and stirring the reaction mixture for 20 h at rt. Title compound: ESI-MS: 672.1 [M+H]+; TLC: Rf=0.45 (DCM/MeOH, 9:1).

Workup

  1. customThe title compound was prepared in analogy to the procedure

Sources & evidence

ORD record
ord-7f7fd1eb607a4786bed7dcc6ee000dcb
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

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