Dimethylformamide → cyclohexyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate

HRID 1154450Notes

Reaction equation

HRID 1154450 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C)C=O.[H-].[Na+].[Cl:15][C:16]1[C:21]2[C:22](=[O:40])[N:23]3[CH2:39][CH2:38][CH2:37][C@H:24]3[C:25]3[N:26]([CH:27]=[N:28][C:29]=3[C:30](N3C=CN=C3)=[O:31])[C:20]=2[CH:19]=[CH:18][CH:17]=1>O>[Cl:15][C:16]1[C:21]2[C:22](=[O:40])[N:23]3[CH2:39][CH2:38][CH2:37][C@H:24]3[C:25]3[N:26]([CH:27]=[N:28][C:29]=3[C:30]([O:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:31])[C:20]=2[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 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 54094222cyclohexyl (S)-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 962WaterSolvent

Procedure

A mixture of 601 mg (6 mmol) of cyclohexanol, 10 ml of dimethylformamide and 288 mg (6 mmol) of sodium hydride (55 percent oil dispersion) is stirred at room temperature for 0.5 hour, the solution obtained is treated with 2.20 g (6 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 a further 0.5 hour and then poured into about 70 ml of water. The precipitated material is filtered off under suction, washed with water and dried. By recrystallization from ethyl acetate there is obtained cyclohexyl (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 166°-167°.

Workup

  1. customthe solution obtained
  2. stirringthe mixture is stirred at room temperature for a further 0.5 hour
  3. filtrationThe precipitated material is filtered off under suction
  4. washwashed with water
  5. customdried
  6. customBy recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-9cbbf33ba0664b34abe0d70f41cbe720
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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