Sodium amide → HCID 53714193, compound

HRID 1606960Notes

Reaction equation

HRID 1606960 reaction equation
[NH2-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][C:7]2[N:13]3[CH:14]=[N:15][C:16]([CH:17]=O)=[C:12]3[CH2:11][N:10]([CH3:19])[C:9](=[O:20])[C:8]=2[CH:21]=1>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CCC.O1CCCC1>[F:3][C:4]1[CH:5]=[CH:6][C:7]2[N:13]3[CH:14]=[N:15][C:16]([CH:17]=[CH:5][CH2:4][CH2:21][CH3:8])=[C:12]3[CH2:11][N:10]([CH3:19])[C:9](=[O:20])[C:8]=2[CH:21]=1

Participants

5

Reactant 2

HCID 24533Sodium amideHCID 198515378-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxaldehyde

Product 1

HCID 53714193HCID 53714193, compound

Reagents, catalysts & solvents 2

HCID 159628Butyltriphenylphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

40.70 g of an equimolar mixture of butyltriphenylphosphonium bromide and sodium amide was stirred at room temperature for 15 minutes in 150 ml of tetrahydrofuran. 20.73 g (80 mmol) of 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxaldehyde was then added thereto, the mixture was stirred at room temperature for a further 1.5 hours, filtered and the filtrate was evaporated. After chromatography of the residue on silica gel while eluting with cyclohexane/ether/isopropanol (3:3:1) and recrystallization from ethyl acetate and n-hexane there was obtained 8-fluoro-4,5-dihydro-5-methyl-3-(1-pentenyl)-6H-imidazo[1,5-a][1,4]-benzodiazepin-6-one of melting point 150°-151°.

Workup

  1. filtrationfiltered
  2. customthe filtrate was evaporated
  3. washAfter chromatography of the residue on silica gel while eluting with cyclohexane/ether/isopropanol (3:3:1) and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-bf7e0c77f5af46118c99c1ae67c38f24
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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