Water → HCID 12971640, compound

HRID 1954686Notes

Reaction equation

HRID 1954686 reaction equation
[H-].[Na+].[CH3:3][N:4]1[CH2:13][CH2:12][C:11]2[C:10]([C:14]3[CH:19]=[CH:18][C:17]([S:20](=[O:25])(=[O:24])[N:21]([CH3:23])[CH3:22])=[CH:16][CH:15]=3)=[CH:9][C:8]3[C:26](=[O:30])[C:27](=[O:29])[NH:28][C:7]=3[C:6]=2[CH2:5]1.[CH3:31]I.O>CN(C)C=O>[CH3:31][N:28]1[C:7]2[C:6]3[CH2:5][N:4]([CH3:3])[CH2:13][CH2:12][C:11]=3[C:10]([C:14]3[CH:19]=[CH:18][C:17]([S:20](=[O:25])(=[O:24])[N:21]([CH3:22])[CH3:23])=[CH:16][CH:15]=3)=[CH:9][C:8]=2[C:26](=[O:30])[C:27]1=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11538568HCID 11538568, compound

Product 1

HCID 12971640HCID 12971640, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

NaH 60% (110 mg, 2.8 mmol) was added at 0° C. to a mixture of 8-methyl-5-(4-(N,N-dimethylsulfamoyl)phenyl)-6,7,8,9-tetrahydro-1-H-pyrrolo[3,2-h]isoquinoline-2,3-dione (1 g, 2.5 mmol) in dimethylformamide (10 ml). The mixture was stirred at 0° C. for 10 min. Methyliodide (175 μl, 2.8 mmol) was added and the mixture was stirred or one hour at ambient temperature. The reaction mixture was poured into water (20 ml) and extracted with ethyl acetate (2×25 ml). The organic phase was dried over sodium sulphate and evaporated. Pure 1-methyl-8-methyl-5-(4-(N,N-dimethylsulfamoyl)phenyl)-6,7,8,9-tetrahydro-pyrrolo[3,2-h]isoquinoline-2,3-dione was obtained after purification on silica gel using dichloromethane/acetone/methanol (8:1:1) as the eluent. Yield 160 mg, m.p. 232-240° C. (decomposes).

Workup

  1. stirringthe mixture was stirred or one hour at ambient temperature
  2. extractionextracted with ethyl acetate (2×25 ml)
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-9b1fd215f6ee4a5cae65c0ef439067ca
Source dataset
uspto-grants-2000_09
Patent number
US06124285

Reaction notes

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