N-bromobutanimide → (S)-(9-bromo-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-(3-chloro-5-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amine

HRID 507180Notes

Reaction equation

HRID 507180 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:5][N:6]([C:23]1[N:24]=[N:25][N:26]([CH3:28])[N:27]=1)[C@H:7]1[CH2:13][CH2:12][CH2:11][NH:10][C:9]2[CH:14]=[C:15]([C:19]([F:22])([F:21])[F:20])[C:16]([CH3:18])=[CH:17][C:8]1=2.[Br:36]N1C(=O)CCC1=O>C(O)(=O)C>[Br:36][C:14]1[C:9]2[NH:10][CH2:11][CH2:12][CH2:13][C@H:7]([N:6]([CH2:5][C:4]3[CH:29]=[C:30]([C:32]([F:35])([F:33])[F:34])[CH:31]=[C:2]([Cl:1])[CH:3]=3)[C:23]3[N:24]=[N:25][N:26]([CH3:28])[N:27]=3)[C:8]=2[CH:17]=[C:16]([CH3:18])[C:15]=1[C:19]([F:20])([F:21])[F:22]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59432495(S)-(3-chloro-5-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-(7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine-5-yl)-amine

Product 1

HCID 59432411(S)-(9-bromo-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-(3-chloro-5-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amineYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Stir (S)-(3-chloro-5-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-(7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine-5-yl)-amine (0.53 g, 1.02 mmol) with N-bromosuccinimide (0.22 g, 1.22 mmol) in acetic acid (2 mL) at room temperature for 2 h. Evaporate the solvent under reduced pressure. Dilute the residue with water and neutralize with saturated NaHCO3 and extract with EtOAc (3×25 mL). Combine the organic layers and wash with water and brine, dry over sodium sulfate, filter, and concentrate under reduced pressure to give a residue. Purify the residue by flash chromatography, eluting with hexane/ethyl acetate (5-40% EtOAc in hexane), to provide the title compound (0.49 g, 83%). MS (ES+): 599 (M+H).

Workup

  1. customEvaporate the solvent under reduced pressure
  2. additionDilute the residue with water
  3. extractionextract with EtOAc (3×25 mL)
  4. washCombine the organic layers and wash with water and brine
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. customto give a residue
  9. customPurify the residue by flash chromatography
  10. washeluting with hexane/ethyl acetate (5-40% EtOAc in hexane)

Sources & evidence

ORD record
ord-2abe48391c864c81bec8887cac587df1
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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