Cyanogen Bromide → (+/-)-Isopropyl 5-[(3,5-bistrifluoromethyl-benzyl)-cyano-amino]-8-chloro-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate

HRID 507060Notes

Reaction equation

HRID 507060 reaction equation
[N:1]#[C:2]Br.[F:4][C:5]([F:37])([F:36])[C:6]1[CH:7]=[C:8]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:9][NH:10][CH:11]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[C:13]2[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:12]1=2>CCOCC>[F:37][C:5]([F:4])([F:36])[C:6]1[CH:7]=[C:8]([CH:29]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:31]=1)[CH2:9][N:10]([C:2]#[N:1])[CH:11]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[C:13]2[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:12]1=2

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 59432446Isopropyl 5-(3,5-bistrifluoromethyl-benzylamino)-8-chloro-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate

Product 1

HCID 59432310(+/-)-Isopropyl 5-[(3,5-bistrifluoromethyl-benzyl)-cyano-amino]-8-chloro-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylateYield 60.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Add a solution of cyanogen bromide (68 mg, 0.63 mmol) in ether (2.6 mL) to a solution of isopropyl 5-(3,5-bistrifluoromethyl-benzylamino)-8-chloro-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (512 mg, 1.0 mmol) in ether (2.6 mL). Stir the mixture overnight at room temperature. Filter off the resulting solid and wash with ether. Wash the filtrate with water, dry over anhydrous sodium sulfate, filter and remove the solvent under reduced pressure. Purify the residue by flash chromatography, eluting with hexanes/ethyl acetate, to afford the title compound (204 mg, 38%): MS (ES+): 534 (M+H).

Workup

  1. filtrationFilter off the resulting solid
  2. washwash with ether
  3. washWash the filtrate with water
  4. dry with materialdry over anhydrous sodium sulfate
  5. filtrationfilter
  6. customremove the solvent under reduced pressure
  7. customPurify the residue by flash chromatography
  8. washeluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-dddc072f72574e14aa5aa6ab06197f8e
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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