Phenyl isocyanate → 6-hydroxy-6-phenethyl-N-phenyl-7-(trifluoromethyl)-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-hi]indole-2(1H)-carboxamide

HRID 1505724Notes

Reaction equation

HRID 1505724 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.[CH2:17]([C:25]1([OH:42])[CH:33]=[C:32]2[CH2:34][NH:35][CH2:36][CH2:37][N:30]3[C:31]2=[C:27]([CH:28]=[CH:29]3)[CH:26]1[C:38]([F:41])([F:40])[F:39])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>C1COCC1>[OH:42][C:25]1([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:33]=[C:32]2[CH2:34][NH:35][CH:36]([C:8]([NH:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:9])[CH2:37][N:30]3[C:31]2=[C:27]([CH:28]=[CH:29]3)[CH:26]1[C:38]([F:41])([F:40])[F:39]

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 866919906-Phenethyl-7-(trifluoromethyl)-1,2,3,4,6,7-hexahydro-[1,4]diazepino[6,7,1-hi]indol-6-ol trifluoroacetate

Product 1

HCID 866919946-hydroxy-6-phenethyl-N-phenyl-7-(trifluoromethyl)-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-hi]indole-2(1H)-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Phenyl isocyanate (3.8 mg, 0.05 mmol) was added to a solution of 6-phenethyl-7-(trifluoromethyl)-1,2,3,4,6,7-hexahydro-[1,4]diazepino[6,7,1-hi]indol-6-ol trifluoroacetate (14 mg, 0.039 mmol) in THF (3 mL) containing triethylamine (11 mg, 0.11 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 30 min, then stirred at room temperature overnight. The resulting mixture was concentrated under reduced pressure, the residue dissolved in ethyl acetate and the resulting solution was washed sequentially with water, NaHCO3 (sat'd. aq) and brine. The organic phase was dried (Na2SO4) and concentrated to yield 6-hydroxy-6-phenethyl-N-phenyl-7-(trifluoromethyl)-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-hi]indole-2(1H)-carboxamide (MH+=482).

Workup

  1. stirringstirred at room temperature overnight
  2. concentrationThe resulting mixture was concentrated under reduced pressure
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washthe resulting solution was washed sequentially with water, NaHCO3 (sat'd. aq) and brine
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5004e33a89704605a47c5d8c402f1683
Source dataset
uspto-grants-2015_12
Patent number
US09216998B2

Reaction notes

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