Dichloromethane → 8-(2,6-Difluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid [5-(3,3,4-trimethyl-piperazin-1-ylmethyl)-pyridin-2-yl]-amide

HRID 2391875Notes

Reaction equation

HRID 2391875 reaction equation
C(O[C:4]([C:6]1[C:7]2[N:8]=[CH:9][CH:10]=[N:11][C:12]=2[C:13]([C:16]2[C:21]([F:22])=[C:20]([O:23][CH3:24])[CH:19]=[C:18]([O:25][CH3:26])[C:17]=2[F:27])=[CH:14][CH:15]=1)=[O:5])C.[CH3:28][C:29]1([CH3:44])[N:34]([CH3:35])[CH2:33][CH2:32][N:31]([CH2:36][C:37]2[CH:38]=[CH:39][C:40]([NH2:43])=[N:41][CH:42]=2)[CH2:30]1.C([O-])(O)=O.[Na+].C(Cl)Cl>C(Cl)Cl.CO>[CH3:28][C:29]1([CH3:44])[N:34]([CH3:35])[CH2:33][CH2:32][N:31]([CH2:36][C:37]2[CH:38]=[CH:39][C:40]([NH:43][C:4]([C:6]3[C:7]4[N:8]=[CH:9][CH:10]=[N:11][C:12]=4[C:13]([C:16]4[C:17]([F:27])=[C:18]([O:25][CH3:26])[CH:19]=[C:20]([O:23][CH3:24])[C:21]=4[F:22])=[CH:14][CH:15]=3)=[O:5])=[N:41][CH:42]=2)[CH2:30]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 552164065-[(3,3,4-Trimethyl-1-piperazinyl)methyl]-2-pyridinamineHCID 866411458-(2,6-Difluoro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid ethyl ester

Product 1

HCID 445144648-(2,6-Difluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid [5-(3,3,4-trimethyl-piperazin-1-ylmethyl)-pyridin-2-yl]-amide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared in analogy to the procedure described in Example 115 but using 8-(2,6-difluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid ethyl ester (Step 124.1), 5-(3,3,4-trimethyl-piperazin-1-ylmethyl)-pyridin-2-ylamine (Step 107.1), stirring the reaction mixture for 15 min at reflux, pouring it onto a saturated aqueous solution of NaHCO3 and DCM. Title compound: ESI-MS: 563.1 [M+H]+; tR=3.72 min (System 1); TLC: Rf=0.33 (DCM/MeOH/NH3aq, 94:5:1).

Workup

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

Sources & evidence

ORD record
ord-b1c75ad6ee994eee97f5c729c1d68f4a
Source dataset
uspto-grants-2012_09
Patent number
US08273882B2

Reaction notes

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