Triethylamine → 1-oxo-N-[3-(1-trityl-1H-imidazol-4-yl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxamide

HRID 1748352Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1748352
[O:1]=[C:2]1[C:8]2=[CH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]([OH:18])=O)=[CH:14][C:15]=3[N:7]2[CH2:6][CH2:5][CH2:4][NH:3]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.[C:52]([N:71]1[CH:75]=[C:74]([C:76]2[CH:77]=[C:78]([CH:80]=[CH:81][CH:82]=2)[NH2:79])[N:73]=[CH:72]1)([C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1.C(N(CC)CC)C>CN(C=O)C.O>[O:1]=[C:2]1[C:8]2=[CH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]([NH:79][C:78]4[CH:80]=[CH:81][CH:82]=[C:76]([C:74]5[N:73]=[CH:72][N:71]([C:52]([C:65]6[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=6)([C:59]6[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=6)[C:53]6[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=6)[CH:75]=5)[CH:77]=4)=[O:18])=[CH:14][C:15]=3[N:7]2[CH2:6][CH2:5][CH2:4][NH:3]1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 114751133-(1-trityl-1H-imidazol-4-yl)anilineHCID 672357061-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid2×

Produkt 1

HCID 683235541-oxo-N-[3-(1-trityl-1H-imidazol-4-yl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid (Intermediate J, 61 mg, 0.25 mmol) in DMF (1.5 mL) is added benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (194 mg, 0.37 mmol). The reaction mixture is stirred for 10 min and 3-(1-trityl-1H-imidazol-4-yl)aniline (100 mg, 0.25 mmol) and triethylamine (0.07 mL, 0.50 mmol) are added. The reaction mixture is stirred at room temperature for 16 h. Water (35 mL) is added and the resulting solid is collected by filtration and rinsed with water to afford the title crude compound which is used in the next step without purification.

Aufarbeitung

  1. stirringThe reaction mixture is stirred at room temperature for 16 h
  2. filtrationthe resulting solid is collected by filtration
  3. washrinsed with water

Quellen und Nachweise

ORD-Eintrag
ord-487920a234e647e28ddda1ea997046bd
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150577B2

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