Triethylamine → 2-Methyl-cyclopropanecarboxylic acid (6-oxo-2-phenyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-amide

HRID 2375030Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2375030
C(N(CC)CC)C.[NH2:8][C:9]1[CH:10]=[C:11]2[C:27](=[O:28])[NH:26][N:25]=[CH:24][C:13]3=[C:14]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[NH:15][C:16]([CH:17]=1)=[C:12]23.[CH3:29][CH:30]1[CH2:32][CH:31]1[C:33](O)=[O:34].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:28]=[C:27]1[C:11]2[C:12]3[C:13](=[C:14]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[NH:15][C:16]=3[CH:17]=[C:9]([NH:8][C:33]([CH:31]3[CH2:32][CH:30]3[CH3:29])=[O:34])[CH:10]=2)[CH:24]=[N:25][NH:26]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 998732-Methylcyclopropanecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1357740798-Amino-2-phenyl-1,5-dihydro-[1,2]diazepino[4,5,6-cd]indol-6-one

Produkt 1

HCID 1361417852-Methyl-cyclopropanecarboxylic acid (6-oxo-2-phenyl-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-amideAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Triethylamine (0.030 mL, 0.22 mmol), the title compound of Example 7 (15 mg, 0.054 mmol) and 2-methyl-cyclopropanecarboxylic acid (6 mg, 0.062 mmol) were stirred in N,N-dimethylformamide (1.0 mL). O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (25 mg, 0.065 mmol) was added and the reaction was stirred overnight at which point the volatile components were removed under vacuum. The resulting mixture was purified on silica gel, eluting with 3:2 hexane:ethyl acetate. The purest fractions were combined and after solvent removal, the resulting solids were triturated with diethyl ether to give the title compound (7 mg, 0.020 mmol) as yellow powder in 36% yield.

Aufarbeitung

  1. customwere removed under vacuum
  2. customThe resulting mixture was purified on silica gel
  3. washeluting with 3:2 hexane
  4. customafter solvent removal
  5. customthe resulting solids were triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-ba5e2a05729248e58100294838ae3c87
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07462713B2

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