Dimethylamine, hydrochloride → HCID 23293135, compound

HRID 378722Notes

Reaction equation

HRID 378722 reaction equation
[CH:1]([CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([NH:24][C:25]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=2)=[O:26])([CH2:13][C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)=[O:15])[C:5]1=[O:36])=O.Cl.[CH3:38][NH:39][CH3:40].C([BH3-])#N.[Na+]>CO>[CH3:35][O:34][C:30]1[CH:29]=[C:28]([NH:27][C:25](=[O:26])[NH:24][C:6]2([CH2:13][C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=3)=[O:15])[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:4]([CH2:3][CH2:1][N:39]([CH3:40])[CH3:38])[C:5]2=[O:36])[CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 22013058(RS)-1-(Formylmethyl)-3-(N'-(3-methoxyphenyl)ureido)-3-((4-methylphenyl)aminocarbonylmethyl)indolin-2-one

Product 1

HCID 23293135HCID 23293135, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.386 g of (RS)-1-(formylmethyl)-3-(N'-(3-methoxyphenyl)ureido)-3-((4-methylphenyl)aminocarbonylmethyl)indolin-2-one in 50 ml of methanol was added 0.8 g of dimethylamine hydrochloride at room temperature, and 1.0 g of sodium cyanoborohydride was then added thereto. The mixture was stirred at room temperature for 1 day, followed by concentration. The concentrate was diluted with dichloromethane and washed with an aqueous solution of sodium chloride. The organic layer was dried over anhydrous sodium sulfate and concentrated. The crude product was washed with dichloromethane to afford 0.107 g (26%) of the title compound.

Workup

  1. concentrationfollowed by concentration
  2. additionThe concentrate was diluted with dichloromethane
  3. washwashed with an aqueous solution of sodium chloride
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. washThe crude product was washed with dichloromethane

Sources & evidence

ORD record
ord-2e9514130f1a4fc4b95db78cac75495e
Source dataset
uspto-grants-2000_02
Patent number
US06031111

Reaction notes

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