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 1505724노트

반응식

HRID 1505724 반응식
[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]

참가 물질

5

반응물 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

생성물 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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5004e33a89704605a47c5d8c402f1683
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216998B2

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