3-Pyrrolidone, 1-methyl- → n-{4-Methyl-3-[(4-(3-pyridyl)pyrimidin-2-yl)amino]phenyl}{4-[(1-methylpyrrolidin-3-yl)amino]phenyl}carboxamide

HRID 1766992Notes

Reaction equation

HRID 1766992 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([NH:20][C:21]3[N:26]=[C:25]([C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)[CH:24]=[CH:23][N:22]=3)[CH:14]=2)=[O:11])=[CH:6][CH:5]=1)([O-])=O.[CH3:33][N:34]1[CH2:38][CH2:37][C:36](=O)[CH2:35]1>CCO>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:10]([C:7]2[CH:8]=[CH:9][C:4]([NH:1][CH:36]3[CH2:37][CH2:38][N:34]([CH3:33])[CH2:35]3)=[CH:5][CH:6]=2)=[O:11])=[CH:14][C:15]=1[NH:20][C:21]1[N:26]=[C:25]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[CH:24]=[CH:23][N:22]=1

Participants

4

Reactant 2

HCID 1442833-Pyrrolidone, 1-methyl-HCID 54764679(4-Nitrophenyl)-n-{4-methyl-3-[(4-(3-pyridyl)pyrimidin-2-yl)-amino]phenyl}-carboxamide

Product 1

HCID 11202429n-{4-Methyl-3-[(4-(3-pyridyl)pyrimidin-2-yl)amino]phenyl}{4-[(1-methylpyrrolidin-3-yl)amino]phenyl}carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above nitro compound was hydrogenated under hydrogen atomosphere in EtOH for 1 hour and filtered through Celite. To the solution was added NaBHCN (1.3 eq) and 1-methyl-3-pyrrolidinone (1 eq), the reaction was stirred at RT overnight and evaporated in vacuo and further purified by flash chromatography on silica gel afforded title compound. Mass: (M+1), 480.

Workup

  1. filtrationfiltered through Celite
  2. customevaporated in vacuo
  3. customfurther purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-dd281258df544c4588163946c368d256
Source dataset
uspto-grants-2007_06
Patent number
US07232825B2

Reaction notes

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