Methyl iodide → HCID 19851583, compound

HRID 1606994Notes

Reaction equation

HRID 1606994 reaction equation
[OH-:1].[K+].[Cl:3][C:4]1[C:9]2[CH2:10][N:11]([CH3:27])[CH2:12][C:13]3[N:14]([C:15](=O)[NH:16][C:17]=3[C:18]#[C:19][C:20]3([OH:25])[CH2:24][CH2:23][CH2:22][CH2:21]3)[C:8]=2[CH:7]=[CH:6][CH:5]=1.[CH3:28]I>CS(C)=O>[Cl:3][C:4]1[C:9]2[C:10](=[O:1])[N:11]([CH3:27])[CH2:12][C:13]3[N:14]([CH:15]=[N:16][C:17]=3[C:18]#[C:19][C:20]3([O:25][CH3:28])[CH2:21][CH2:22][CH2:23][CH2:24]3)[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 70394415HCID 70394415, compound

Product 1

HCID 19851583HCID 19851583, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

2.35 g (42 mmol) of freshly powdered potassium hydroxide was stirred in 30 ml of dimethyl sulfoxide for 5 minutes. There were then added in succession 4.0 g (11.25 mmol) of 7-chloro-4,5-dihydro-3-[(1-hydroxycyclopentyl)ethynyl]-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepine-one and 3.12 g (22.5 mmol) of methyl iodide and the mixture was stirred for a further 1 hour before the dimethyl sulfoxide was removed by evaporation. The residue was taken up in water and extracted three times with methylene chloride. The combined organic extracts were dried over magnesium sulphate, evaporated and the residue was chromatographed on silica gel while eluting with ethyl acetate/hexane (1:1). After recrystallization from ethyl acetate there was obtained 7-chloro-4,5-dihydro-3-[(1-methoxycyclopentyl)ethynyl]-5-methyl-6H-imidazo[1,5-a][1,4]-benzodiazepin-6-one of melting point 174°-175°.

Workup

  1. customwas removed by evaporation
  2. extractionextracted three times with methylene chloride
  3. dry with materialThe combined organic extracts were dried over magnesium sulphate
  4. customevaporated
  5. customthe residue was chromatographed on silica gel
  6. washwhile eluting with ethyl acetate/hexane (1:1)
  7. customAfter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-f721e7f7b860459eab66e4fbca531e53
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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