N-bromobutanimide → HCID 59432473, compound

HRID 507158Notes

Reaction equation

HRID 507158 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]([F:46])([F:45])[C:11]1[CH:12]=[C:13]([CH:38]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:40]=1)[CH2:14][N:15]([C:32]1[N:33]=[N:34][N:35]([CH3:37])[N:36]=1)[C@H:16]1[CH2:22][CH2:21][CH2:20][NH:19][C:18]2[CH:23]=[C:24]([C:28]([F:31])([F:30])[F:29])[C:25]([CH3:27])=[CH:26][C:17]1=2>C(O)(=O)C>[F:46][C:10]([F:45])([F:9])[C:11]1[CH:12]=[C:13]([CH:38]=[C:39]([C:41]([F:44])([F:42])[F:43])[CH:40]=1)[CH2:14][N:15]([C@H:16]1[CH2:22][CH2:21][CH2:20][NH:19][C:18]2[C:23]([Br:1])=[C:24]([C:28]([F:29])([F:30])[F:31])[C:25]([CH3:27])=[CH:26][C:17]1=2)[C:32]1[N:33]=[N:34][N:35]([CH3:37])[N:36]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59432408(S)-(3,5-bistrifluoromethylbenzyl)-(2-methyl-2H-tetrazol-5-yl)-(7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)amine

Product 1

HCID 59432473HCID 59432473, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Add N-bromosuccinimide (1.10 g, 6.19 mmol) in one portion to a solution of (S)-(3,5-bistrifluoromethylbenzyl)-(2-methyl-2H-tetrazol-5-yl)-(7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)amine (2.85 g, 5.16 mmol) (Example 3, Step 18) in acetic acid (25 mL) at room temperature. Stir for 2 hours. Evaporate the solvent under reduced pressure. Partition the residue between ethyl acetate (250 mL) and aqueous Na2CO3 (250 mL). Separate the layers, dry over Na2SO4, filter and concentrate. Purify the residue by column chromatography on silica gel, eluting with ethyl acetate/hexanes (0-30%), to provide the title compound as an off-white solid (2.99 g, 92%). MS (ES+): 631, 633 (M+H).

Workup

  1. customEvaporate the solvent under reduced pressure
  2. customPartition the residue between ethyl acetate (250 mL) and aqueous Na2CO3 (250 mL)
  3. customSeparate the layers
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the residue by column chromatography on silica gel
  8. washeluting with ethyl acetate/hexanes (0-30%)

Sources & evidence

ORD record
ord-beb5d3e94bb14a238cc285b822a440b0
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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