Benzoyl Peroxide → HCID 59253027, compound

HRID 884753Notes

Reaction equation

HRID 884753 reaction equation
[C:1]([O:5][C:6](=[O:39])[N:7]([N:11]1[C:20]([CH3:21])=[C:19]([C:22](=[O:36])[NH:23][C@@H:24]([CH:32]2[CH2:35][CH2:34][CH2:33]2)[C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)[C:18]2[C:13](=[C:14]([F:37])[CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:38])[CH2:8][CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2].[Br:40]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:39])[N:7]([N:11]1[C:20]([CH2:21][Br:40])=[C:19]([C:22](=[O:36])[NH:23][C@@H:24]([CH:32]2[CH2:35][CH2:34][CH2:33]2)[C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)[C:18]2[C:13](=[C:14]([F:37])[CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:38])[CH2:8][CH2:9][CH3:10])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 67298064HCID 67298064, compound

Product 1

HCID 59253027HCID 59253027, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

(4-{[(S)-Cyclobutyl-(3-fluoro-phenyl)-methyl]carbamoyl}-8-fluoro-3-methyl-1-oxo-1H-isoquinolin-2-yl)-propyl-carbamicacid tert-butyl ester (0.2 g, 0.4 mmol; prepared as described in example 8), carbon tetrachloride (50 mL), N-bromosuccinimide (0.072 g, 0.41 mmol) and benzoyl peroxide (10 mg, 0.04 mmol) are warmed at 80° C. for 2 hours. The reaction mixture was cooled and washed with 10 ml of water. The organic phase was dried over MgSO4 and was rotovaped to give 0.3 g. crude product. The product was chromatographed on silica gel with Etac:Hept, 30:70 as eluent to give 0.15 g. the title compound as an oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with 10 ml of water
  3. dry with materialThe organic phase was dried over MgSO4
  4. customto give 0.3 g
  5. customThe product was chromatographed on silica gel with Etac
  6. customHept, 30:70 as eluent to give 0.15 g

Sources & evidence

ORD record
ord-3bab313f8fc5400ca68a1bf2a8c366d5
Source dataset
uspto-grants-2012_08
Patent number
US08242134B2

Reaction notes

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