Triethylamine → n-(6-Oxo-2-phenyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-2-tetrazol-1-yl-acetamide

HRID 2375031Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2375031
[NH2:1][C:2]1[CH:3]=[C:4]2[C:20](=[O:21])[NH:19][N:18]=[CH:17][C:6]3=[C:7]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[NH:8][C:9]([CH:10]=1)=[C:5]23.[N:22]1([CH2:27][C:28](O)=[O:29])[CH:26]=[N:25][N:24]=[N:23]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O>[O:21]=[C:20]1[C:4]2[C:5]3[C:6](=[C:7]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)[NH:8][C:9]=3[CH:10]=[C:2]([NH:1][C:28](=[O:29])[CH2:27][N:22]3[CH:26]=[N:25][N:24]=[N:23]3)[CH:3]=2)[CH:17]=[N:18][NH:19]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 5432071-Tetrazolylacetic acid2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 1357740798-Amino-2-phenyl-1,5-dihydro-[1,2]diazepino[4,5,6-cd]indol-6-one

Produkt 1

HCID 135546089n-(6-Oxo-2-phenyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-2-tetrazol-1-yl-acetamideAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Preparation of example 12 from the title compound of Example 7 (15 mg, 0.054 mmol), tetrazol-1-yl-acetic acid (8 mg, 0.062 mmol), triethylamine (0.030 mL, 0.22 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (25 mg, 0.065 mmol) in N,N-dimethylformamide (1.0 mL) was carried out analogously to Example 11. Additional tetrazol-1-yl-acetic acid (1.0 mg, 0.008 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (3.0 mg, 0.008 mmol) were added after c.a. 18 hours to drive the reaction to completion. Filtration, concentration and recrystallization afforded the title compound (12 mg, 0.031 mmol) as a yellow powder in 58% yield.

Aufarbeitung

  1. custom18 hours
  2. customthe reaction to completion
  3. filtrationFiltration, concentration and recrystallization

Quellen und Nachweise

ORD-Eintrag
ord-5063a2fbb18044ffb8267568771c9e5c
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07462713B2

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