Water → HCID 18634702, compound

HRID 1606965Notes

Reaction equation

HRID 1606965 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:21])[N:9]3[CH2:20][CH2:19][CH2:18][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]#[CH:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:24]I.O>CN(C)C=O.CCCCCC>[Cl:1][C:2]1[C:7]2[C:8](=[O:21])[N:9]3[CH2:20][CH2:19][CH2:18][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]#[C:17][CH3:24])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 54397252HCID 54397252, compound

Product 1

HCID 18634702HCID 18634702, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

250 mg (0.85 mmol) of (S)-8-chloro-1-ethynyl-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one was suspended in 5 ml of N,N-dimethylformamide. 50 mg (1 mmol) of sodium hydride dispersion (55% in oil) was washed with n-hexane and then introduced into the above suspension. After 10 minutes 0.1 ml (1.5 mmol) of methyl iodide was added thereto and the mixture was stirred at room temperature for a further 4.5 hours. The mixture was poured into 50 ml of water and extracted four times with methylene chloride. The organic extracts were washed four times with water, dried over magnesium sulphate and evaporated. After chromatography of the residue on silica gel while eluting with ethyl acetate and recrystallization from ethyl acetate and hexane there was obtained (S)-8-chloro-11,12,13,13a-tetrahydro-1-propynyl-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one of melting point 205°-20°.

Workup

  1. additionintroduced into the above suspension
  2. extractionextracted four times with methylene chloride
  3. washThe organic extracts were washed four times with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. washAfter chromatography of the residue on silica gel while eluting with ethyl acetate and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-e9882c9d31dd409bb026fcae78d936e0
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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