Bromopinacolone → HCID 54420953, compound

HRID 1979491Notes

Reaction equation

HRID 1979491 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:6]=2[N:5]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:4][C@H:3]1[NH:20][C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:26][CH:25]=1)=[O:22].[H-].[Na+].Br[CH2:40][C:41]([C:43]([CH3:46])([CH3:45])[CH3:44])=[O:42]>CN(C)C=O>[C:43]([C:41]([CH2:40][N:8]1[C:7]2[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:6]=2[N:5]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:4][C@@H:3]([NH:20][C:21]([NH:23][C:24]2[CH:25]=[CH:26][C:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:28][CH:29]=2)=[O:22])[C:2]1=[O:1])=[O:42])([CH3:46])([CH3:45])[CH3:44]

Participants

5

Reactant 3

HCID 21642BromopinacoloneHCID 24758Sodium hydrideHCID 54063423HCID 54063423, compound

Product 1

HCID 54420953HCID 54420953, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

(R)-1-(2-oxo-5-cyclohexyl-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)-3-(4-tert-butoxycarbonylphenyl)urea (500 mg) was dissolved in N,N-dimethylformamide (5 ml), the solution was cooled to internal temperature 5° C. Under argon atmosphere, 60% sodium hydride (49 mg) was added, the mixture was stirred at internal temperature 5° C. for 30 minutes. Bromomethyl tert-butylketone (218 mg) was added thereto, stirred at internal temperature 5° C. for one hour. The reaction mixture was poured into ice-water, extracted with ethyl acetate. The organic layer was successively washed with water and saturated brine, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform), to thereby obtain 200 mg of the title compound.

Workup

  1. stirringstirred at internal temperature 5° C. for one hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was successively washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-8223c1839a3140c485dfd0fb101d9865
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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