Dichloromethane → HCID 66607332, compound

HRID 905890Notes

Reaction equation

HRID 905890 reaction equation
[CH2:1]([N:3]([CH2:29][CH3:30])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][C:9]2[NH:12][C:13]([CH:16]=[C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([F:26])[CH:24]=4)[NH:19][C:18]3=[O:27])=[C:14]([CH3:15])[C:8]=2[C:7]1=[O:28])[CH3:2].ClCCl.[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]\[C:37]([OH:39])=[O:38]>CO>[C:34]([OH:41])(=[O:40])/[CH:35]=[CH:36]\[C:37]([OH:39])=[O:38].[CH2:29]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][C:9]2[NH:12][C:13]([CH:16]=[C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([F:26])[CH:24]=4)[NH:19][C:18]3=[O:27])=[C:14]([CH3:15])[C:8]=2[C:7]1=[O:28])[CH3:30]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 444266Maleic AcidHCID 666067185-(2-(Diethylamino)ethyl)-2-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-3-methyl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one

Product 1

HCID 66607332HCID 66607332, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred yellow suspension of 5-(2-diethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one (200 mg, 0.49 mmol) obtained form Example 1 in methanol (4 ml) and dichloromethane (8 ml) was added with maleic acid (57 mg, 0.49 mmol) at room temperature. The resulting solution was stirred for 30 minutes. The solvent was evaporated under reduced pressure and the residue was added with 5 ml of acetonitrile. The resulting solution was heated to reflux for 30 minutes, cooled down to room temperature and filtered. The filter cake was washed with cold acetonitrile (0.5 ml×3) and ethanol (0.5 ml×3) and dried in vacuo to give the title compound 5-(2-diethylamino-ethyl)-2-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one maleate (202 mg, 66.2%) as a yellow solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was added with 5 ml of acetonitrile
  3. temperatureThe resulting solution was heated
  4. temperatureto reflux for 30 minutes
  5. filtrationfiltered
  6. washThe filter cake was washed with cold acetonitrile (0.5 ml×3) and ethanol (0.5 ml×3)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-9a38f6c166e748478b2b333be03931db
Source dataset
uspto-grants-2011_09
Patent number
US08012966B2

Reaction notes

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