HCID 68775524, compound → HCID 44156274, compound

HRID 1253877Notes

Reaction equation

HRID 1253877 reaction equation
C1(OC([N:10]2[CH2:16][C:15]3[CH:17]=[C:18]([F:22])[C:19]([F:21])=[CH:20][C:14]=3[NH:13][C:12](=[O:23])[CH2:11]2)=O)C=CC=CC=1>CO.[Pd]>[F:22][C:18]1[C:19]([F:21])=[CH:20][C:14]2[NH:13][C:12](=[O:23])[CH2:11][NH:10][CH2:16][C:15]=2[CH:17]=1

Participants

4

Reactant 1

HCID 68775524HCID 68775524, compound

Product 1

HCID 44156274HCID 44156274, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (7,8-difluoro-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid phenyl ester) (2.64 g, 6.15 mmol) in MeOH (30 mL), was added 10% Pd/C (200 mg, 20% w/w) under argon; The reaction was stirred at r.t. for 5 h under hydrogen atmosphere. After completion of the reaction as confirmed by TLC, the reaction mixture was filtered through celite bed and washings were given with EtOAc and MeOH. The solvents were removed in vacuo to afford the crude compound which was purified by column chromatography (silica gel: 1:9 MeOH:CHCl3) to afford pure 7,8-difluoro-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one as off white solid (0.98 g, 80%).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered through celite bed and washings
  3. customThe solvents were removed in vacuo
  4. customto afford the crude compound which
  5. customwas purified by column chromatography (silica gel: 1:9 MeOH:CHCl3)

Sources & evidence

ORD record
ord-11c68f9f47ae4067afffbde81fded51a
Source dataset
uspto-grants-2013_06
Patent number
US08455479B2

Reaction notes

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