5-((4-Ethylpiperazin-1-yl)methyl)pyridin-2-amine hydrochloride → 8-(2-Chloro-5-methoxy-3,6-dimethyl-phenyl)-quinoxaline-5-carboxylic acid [5-(4-ethyl-piperazin-1-ylmethyl)-pyridin-2-yl]-amide

HRID 2391843Notes

Reaction equation

HRID 2391843 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH3:10])=[C:4]([CH3:11])[C:3]=1[C:12]1[C:21]2[N:20]=[CH:19][CH:18]=[N:17][C:16]=2[C:15]([C:22]([OH:24])=O)=[CH:14][CH:13]=1.Cl.[CH2:26]([N:28]1[CH2:33][CH2:32][N:31]([CH2:34][C:35]2[CH:36]=[CH:37][C:38]([NH2:41])=[N:39][CH:40]=2)[CH2:30][CH2:29]1)[CH3:27]>>[CH2:26]([N:28]1[CH2:29][CH2:30][N:31]([CH2:34][C:35]2[CH:36]=[CH:37][C:38]([NH:41][C:22]([C:15]3[C:16]4[N:17]=[CH:18][CH:19]=[N:20][C:21]=4[C:12]([C:3]4[C:4]([CH3:11])=[C:5]([O:9][CH3:10])[CH:6]=[C:7]([CH3:8])[C:2]=4[Cl:1])=[CH:13][CH:14]=3)=[O:24])=[N:39][CH:40]=2)[CH2:32][CH2:33]1)[CH3:27]

Participants

3

Reactant 2

HCID 669145365-((4-Ethylpiperazin-1-yl)methyl)pyridin-2-amine hydrochlorideHCID 866411438-(2-Chloro-5-methoxy-3,6-dimethyl-phenyl)-quinoxaline-5-carboxylic acid

Product 1

HCID 592928228-(2-Chloro-5-methoxy-3,6-dimethyl-phenyl)-quinoxaline-5-carboxylic acid [5-(4-ethyl-piperazin-1-ylmethyl)-pyridin-2-yl]-amide

Procedure

The title compound was prepared in analogy to the procedure described in Step 14.1 but using 8-(2-chloro-5-methoxy-3,6-dimethyl-phenyl)-quinoxaline-5-carboxylic acid (Step 98.1), 5-(4-ethyl-piperazin-1-ylmethyl)-pyridin-2-ylamine hydrochloride (Step 26.1) and stirring the reaction mixture for 20 h at rt. The crude product was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1). Title compound: ESI-MS: 545.0 [M+H]+; tR=3.91 min (System 1); TLC: Rf=0.23 (DCM/MeOH/NH3aq, 94:5:1).

Workup

  1. customThe crude product was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1)

Sources & evidence

ORD record
ord-b82fc474f1ff4d61be65d6c8986994fd
Source dataset
uspto-grants-2012_09
Patent number
US08273882B2

Reaction notes

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