HCID 22392982, compound → HCID 22392916, compound

HRID 411404Notes

Reaction equation

HRID 411404 reaction equation
C(OC([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]=[CH:26][CH:27]=[CH:28][C:15]=2[N:14]([CH2:29][CH2:30][CH2:31][C:32]([F:35])([F:34])[F:33])[C:13]1=[O:36])=O)C1C=CC=CC=1>C(Cl)Cl>[NH2:11][CH:12]1[N:18]=[C:17]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:16]2[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=2[N:14]([CH2:29][CH2:30][CH2:31][C:32]([F:34])([F:33])[F:35])[C:13]1=[O:36]

Participants

3

Reactant 1

HCID 22392982HCID 22392982, compound

Product 1

HCID 22392916HCID 22392916, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(benzoxycarbonyl)amino-2,3-dihydro-1-(4,4,4-trifluorobutyl)-5-phenyl-1H-1,4-benzodiazepin-2-one (1.42 g, 2.87 mmol) in 50 mL of anhydrous methylene chloride was cooled to 0° C. under nitrogen. A stream of anhydrous HBr gas was slowly bubbled through the solution for 1 h. The bubbler was removed and the reaction was warmed to room temperature under nitrogen. After stirring for 1 h, the reaction was concentrated under vacuum and the residue was redissolved in 10 mL of methylene chloride. The crude HBr salt of the product was precipitated from solution using 90 mL of anhydrous ether and collected by filtration. After washing with ether, the HBr salt was dissolved in methylene chloride and saturated sodium bicarbonate. The layers were separated and the organic layer was extracted with saturated sodium bicarbonate. The combined aqueous layers were then back extracted twice with methylene chloride. The combined organic layers were extracted once with water and dried over sodium sulfate. After concentration under vacuum, 1.06 g (100%) of the product was obtained as a white foam which was carried on without further purification.

Workup

  1. customA stream of anhydrous HBr gas was slowly bubbled through the solution for 1 h
  2. customThe bubbler was removed
  3. concentrationthe reaction was concentrated under vacuum
  4. dissolutionthe residue was redissolved in 10 mL of methylene chloride
  5. customThe crude HBr salt of the product was precipitated from solution
  6. filtrationcollected by filtration
  7. washAfter washing with ether
  8. dissolutionthe HBr salt was dissolved in methylene chloride
  9. customThe layers were separated
  10. extractionthe organic layer was extracted with saturated sodium bicarbonate
  11. extractionThe combined aqueous layers were then back extracted twice with methylene chloride
  12. extractionThe combined organic layers were extracted once with water
  13. dry with materialdried over sodium sulfate
  14. concentrationAfter concentration under vacuum

Sources & evidence

ORD record
ord-4ee3ff0e4bc54d9abc4925564bed19b6
Source dataset
uspto-grants-2003_05
Patent number
US06559141B2

Reaction notes

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