Dichloromethane → HCID 86660127, compound

HRID 2365153Notes

Reaction equation

HRID 2365153 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.[CH3:34][S:35]([OH:38])(=[O:37])=[O:36]>CO>[S:35]([OH:38])(=[O:37])(=[O:36])[CH3:34].[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].[S:35]([OH:38])(=[O:37])(=[O:36])[CH3:34].[CH2:1]([N:3]([CH2:29][CH3:30])[CH2:4][CH2:5][CH:11]1[NH:6][C:7](=[O:28])[C:8]2[C:14]([CH3:15])=[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])[NH:12][C:9]=2[CH2:10]1)[CH3:2]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 6395Methanesulfonic 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 2

HCID 86660126HCID 86660126, compoundHCID 86660127HCID 86660127, compoundYield 140.2%

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 methane sulfonic acid (32 μl, 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 6-(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 mesylate (174 mg, 73.1%) 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-1fdc5fc190bd491691a32b2488f351d1
Source dataset
uspto-grants-2014_04
Patent number
US08697692B2

Reaction notes

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