Dimethylformamide → HCID 23047240, compound

HRID 2107039Notes

Reaction equation

HRID 2107039 reaction equation
[H-].[K+].[CH3:3][N:4]([CH:6]=[O:7])[CH3:5].[CH3:8][CH:9]1[S:14][C:13](=[O:15])[NH:12][N:11]=[C:10]1[C:16]1[CH:17]=[C:18]2C(=[CH:23][CH:24]=1)NC(=O)[C:19]12[CH2:29][CH2:28][CH2:27][CH2:26]1.[CH3:30]I>O>[CH3:30][N:12]1[N:11]=[C:10]([C:16]2[CH:17]=[C:18]3[C:3](=[CH:23][CH:24]=2)[N:4]([CH3:5])[C:6](=[O:7])[C:19]23[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:9]([CH3:8])[S:14][C:13]1=[O:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 82127Potassium hydrideHCID 23047241HCID 23047241, compound

Product 1

HCID 23047240HCID 23047240, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.76 g (19 mmol) washed potassium hydride, 75 ml dry DMF and 3 g (9.5 mmol) 5'-(3,6-dihydro-6-methyl-2-oxo-2H-1,3,4-thiadiazin-5-yl)-spiro-[cyclopentane-1, 3'-[3H]-indol]-2'(1'H)-one (Example 6) were stirred at room temperature during 30mn. 2.8 g (20 mmol) methyliodide were added and the stirring was continued for 1 hr. 150 ml water were added and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate. The crude product was purified by column chromatography on silica (eluent:methylen chloride/methanol: 99.5/0.5).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customThe crude product was purified by column chromatography on silica (eluent:methylen chloride/methanol: 99.5/0.5)

Sources & evidence

ORD record
ord-4ae9f75c498740b4935b557459ea0944
Source dataset
uspto-grants-1990_06
Patent number
US04933336

Reaction notes

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