Dimethylamine, hydrochloride → HCID 23293135, compound

HRID 618558Notes

Reaction equation

HRID 618558 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-82bb959a59db416ab612878b57a149dd
Source dataset
uspto-grants-1999_09
Patent number
US05952511

Reaction notes

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