N-bromobutanimide → HCID 66901659, compound

HRID 1691439Notes

Reaction equation

HRID 1691439 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[C:20]3[C:21]([Cl:25])=[CH:22][CH:23]=[CH:24][C:19]=3[NH:18][C:17]3[N:26]=[C:27]([C:30]([F:33])([F:32])[F:31])[CH:28]=[CH:29][C:16]=3[CH2:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:41])C(=O)C1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[Br:41][C:22]1[CH:23]=[CH:24][C:19]2[NH:18][C:17]3[N:26]=[C:27]([C:30]([F:32])([F:33])[F:31])[CH:28]=[CH:29][C:16]=3[CH2:15][N:14]([S:11]([C:8]3[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=3)(=[O:12])=[O:13])[C:20]=2[C:21]=1[Cl:25]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 66901760HCID 66901760, compound2×

Product 1

HCID 66901659HCID 66901659, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-[(4-tert-butylphenyl)sulfonyl]-7-chloro-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine (intermediate 25, 60 mg, 0.121 mmol) in DCM (1 mL) was added NBS (23.7 mg, 0.133 mmol) and a few drops of TFA. After stirring at rt for 3 h, the reaction mixture was concentrated to dryness, and the residue was dissolved in ether, washed with sodium thiosulfate, water and brine, dried over MgSO4, filtered and concentrated. The residue was purified by reverse phase HPLC to provide the title compound. LC/MS: m/e 574 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. dissolutionthe residue was dissolved in ether
  3. washwashed with sodium thiosulfate, water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-ffdaefdeca9346b5aa89260eeb89a16b
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

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