Bromopinacolone → HCID 21842357, compound

HRID 1737281Notes

Reaction equation

HRID 1737281 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[N:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]2[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:15]=2[NH:14][C:13]1=[O:30])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C2C=CC=CC=2C=CC=N1.[H-].[Na+].Br[CH2:45][C:46](=[O:51])[C:47]([CH3:50])([CH3:49])[CH3:48]>>[CH2:1]([O:8][C:9]([NH:11][CH:12]1[N:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16]2[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:15]=2[N:14]([CH2:45][C:46]([C:47]([CH3:50])([CH3:49])[CH3:48])=[O:51])[C:13]1=[O:30])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 21642BromopinacoloneHCID 24758Sodium hydrideHCID 134664BenzodiazepineHCID 2756245HCID 2756245, compound

Product 1

HCID 21842357HCID 21842357, compoundYield 93%

Procedure

This was prepared from (3RS)-3-benzyloxycarbonylamino-7-chloro-2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (640 mg, 1.46 mmol, prepared by analogy with the Bock benzodiazepine), sodium hydride (62 mg of an 80% dispersion in oil, 2.04 mmol) and 1-bromopinacolone (537 mg, 3 mmol) following the method of Example 1B. The crude product was purified by flash chromatography on silica gel (eluant EtOAc:hexane fr 30:70 v/v) to afford the title compound (700 mg, 93%).

Workup

  1. customThe crude product was purified by flash chromatography on silica gel (eluant EtOAc:hexane fr 30:70 v/v)

Sources & evidence

ORD record
ord-61bf7d7eacc2404db2c86cce95fb0888
Source dataset
uspto-grants-1999_10
Patent number
US05962451

Reaction notes

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