Lactic Acid → HCID 66606717, compound

HRID 905889Notes

Reaction equation

HRID 905889 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:39])(=[O:38])[CH:35]([CH3:37])[OH:36]>CO>[C:34]([OH:39])(=[O:38])[CH:35]([CH3:37])[OH:36].[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 612Lactic AcidHCID 6344DichloromethaneHCID 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 66606717HCID 66606717, compoundYield 88.9%

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 (193 mg, 0.47 mmol) obtained form Example 1 in methanol (8 ml) and dichloromethane (16 ml) was added with lactic acid (40 μl, 0.47 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 10 ml of acetonitrile. The resulting solution was heated to reflux for 45 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 lactate (208 mg, 88.9%) as a yellow solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was added with 10 ml of acetonitrile
  3. temperatureThe resulting solution was heated
  4. temperatureto reflux for 45 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-ded9219acac742cc9fa57d2ba2088da3
Source dataset
uspto-grants-2011_09
Patent number
US08012966B2

Reaction notes

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