Dimethylformamide → HCID 53933367, compound

HRID 1154480Notes

Reaction equation

HRID 1154480 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:26])[N:9]3[CH2:25][CH2:24][CH2:23][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16](N3C=CN=C3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:33][O:34][C:35]1[CH:41]=[CH:40][C:38]([OH:39])=[CH:37][CH:36]=1.CN(C)C=O>O>[Cl:1][C:2]1[C:7]2[C:8](=[O:26])[N:9]3[CH2:25][CH2:24][CH2:23][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:39][C:38]3[CH:40]=[CH:41][C:35]([O:34][CH3:33])=[CH:36][CH:37]=3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 90154-MethoxyphenolHCID 11430Potassium CarbonateHCID 54332091(S)-1-[(8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-1-yl)carbonyl]imidazole

Product 1

HCID 53933367HCID 53933367, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.0 g (8.2 mmol) of (S)-1-[(8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-1-yl)carbonyl]imidazole, 1.59 g (11.5 mmol) of powdered potassium carbonate, 1.43 g (11.5 mmol) of hydroquinone monomethyl ether and 20 ml of dry dimethylformamide is stirred at room temperature for 16 hours, then poured into 60 ml of water and extracted three times with methylene chloride. The organic extracts are washed twice with saturated sodium chloride solution, dried over magnesium sulphate and evaporated. After chromatography on silica gel while eluting with ethyl acetate and subsequent recrystallization from ethyl acetate there is obtained p-methoxyphenyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate of melting point 210°-211°.

Workup

  1. extractionextracted three times with methylene chloride
  2. washThe organic extracts are washed twice with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. washAfter chromatography on silica gel while eluting with ethyl acetate and subsequent recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-6ffd3f50f56f4e03a7245416002d8906
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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