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 1505724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1505724
[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]

Komponenten

5

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5004e33a89704605a47c5d8c402f1683
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216998B2

Notizen zur Reaktion

Wird geladen…