Water → N-(3-{[(4-cyanophenyl)carbonyl]amino}-2-methylpropyl)-9-ethyl-9H-carbazole-3-carboxamide

HRID 2272596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2272596
[NH2:1][CH2:2][CH:3]([CH3:16])[CH2:4][NH:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1.[CH2:17]([N:19]1[C:31]2[CH:30]=[CH:29][C:28]([C:32](O)=[O:33])=[CH:27][C:26]=2[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH3:18].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O>CN(C=O)C>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([C:6]([NH:5][CH2:4][CH:3]([CH3:16])[CH2:2][NH:1][C:32]([C:28]2[CH:29]=[CH:30][C:31]3[N:19]([CH2:17][CH3:18])[C:20]4[C:25]([C:26]=3[CH:27]=2)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:33])=[O:15])=[CH:8][CH:9]=1)#[N:14]

Komponenten

6

Edukt 4

HCID 962WaterHCID 49128699-Ethyl-9H-carbazole-3-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86729754HCID 86729754, Verbindung

Produkt 1

HCID 86729755N-(3-{[(4-cyanophenyl)carbonyl]amino}-2-methylpropyl)-9-ethyl-9H-carbazole-3-carboxamideAusbeute 50,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of the compound obtained in Step 2 (198 mg, 0.91 mmol), 9-ethyl-9H-carbazole-3-carboxylic acid (218 mg, 0.91 mmol), HATU (450 mg, 1.18 mmol) and TEA (0.381 mL, 2.73 mmol) in DMF (4.5 mL) was stirred at room temperature for 16 hr. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 20 to 100% ethyl acetate/hexane) to give the title compound (200 mg, 0.456 mmol, 50.0%) as a white powder.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer was dried
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 20 to 100% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-1ad407d7127d449391d9c4f71056573e
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120776B2

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