Water → Rac-2-{[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1h-indol-3-yl]-phenyl-amino}-acetamide

HRID 556469Notes

Reaction equation

HRID 556469 reaction equation
Br[C:2]1([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:12].[C:21]1([NH:27][CH2:28][C:29]([NH2:31])=[O:30])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:11][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([N:27]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:28][C:29]([NH2:31])=[O:30])([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)[C:3](=[O:12])[NH:4]2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 153703192-(Phenylamino)acetamideHCID 575072733-Bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one

Product 1

HCID 57479072Rac-2-{[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1h-indol-3-yl]-phenyl-amino}-acetamideYield 13.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of rac-3-bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (370 mg, 1 mmol), 2-phenylamino-acetamide (200 mg, 1.33 mmol) and K2CO3 (300 mg, 2.2 mmol) in DMF (2 mL) was stirred at room temperature for 1 h. The mixture was poured into water (30 ml), extracted with ethyl acetate (10 mL×3). The organic phase was separated, dried over Na2SO4 and concentrated. The residue was purified with chromatography to give 60 mg of rac-2-{[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-phenyl-amino}-acetamide. MS: [M+H]+=439.8.

Workup

  1. extractionextracted with ethyl acetate (10 mL×3)
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified with chromatography

Sources & evidence

ORD record
ord-3c2faf264c614496811b729e78281b43
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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