Water → 1-methyl-cyclopentyl 8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate

HRID 1154456Notes

Reaction equation

HRID 1154456 reaction equation
[CH3:1][C:2]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3]1.[H-].[Na+].[Cl:10][C:11]1[C:16]2[C:17](=[O:35])[N:18]3[CH2:34][CH2:33][CH2:32][C@H:19]3[C:20]3[N:21]([CH:22]=[N:23][C:24]=3[C:25](N3C=CN=C3)=[O:26])[C:15]=2[CH:14]=[CH:13][CH:12]=1.O>CN(C)C=O>[Cl:10][C:11]1[C:16]2[C:17](=[O:35])[N:18]3[CH2:34][CH2:33][CH2:32][CH:19]3[C:20]3[N:21]([CH:22]=[N:23][C:24]=3[C:25]([O:7][C:2]3([CH3:1])[CH2:6][CH2:5][CH2:4][CH2:3]3)=[O:26])[C:15]=2[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 738301-MethylcyclopentanolHCID 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 204348231-methyl-cyclopentyl 8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.2 g (12 mmol) of 1-methyl-cyclopentanol in 25 ml of dry dimethylformamide is treated with 0.5 g (10.3 mmol) of sodium hydride (55% oil dispersion) and to the resulting solution there are added portionwise at -20° 3.79 g (10.3 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. The mixture is stirred at room temperature for 1 hour, poured into about 250 ml of water, the precipitated material is filtered off under suction, washed with water and dried. There is obtained 1-methyl-cyclopentyl 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 190°-191°.

Workup

  1. filtrationthe precipitated material is filtered off under suction
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-ef95ddfca22e478788f97af80ca6d8fa
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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