Pyridine → N-[4-(3-cyano-1-cyclobutyl-6-ethoxy-indol-2-yl)phenyl]morpholine-4-carboxamide

HRID 502234

Reaktionsgleichung

Reaktionsgleichung von HRID 502234
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:22]3[CH2:25][CH2:24][CH2:23]3)[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH2:20][CH3:21])[CH:11]=3)=[CH:4][CH:3]=1.Cl[C:27](OC1C=CC([N+]([O-])=O)=CC=1)=[O:28].N1C=CC=CC=1.[NH:45]1[CH2:50][CH2:49][O:48][CH2:47][CH2:46]1>C(Cl)Cl>[C:17]([C:16]1[C:15]2[C:10](=[CH:11][C:12]([O:19][CH2:20][CH3:21])=[CH:13][CH:14]=2)[N:9]([CH:22]2[CH2:23][CH2:24][CH2:25]2)[C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:27]([N:45]2[CH2:50][CH2:49][O:48][CH2:47][CH2:46]2)=[O:28])=[CH:7][CH:6]=1)#[N:18]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 8083MorpholineHCID 821294-Nitrophenyl chloroformateHCID 250520112-(4-Aminophenyl)-1-cyclobutyl-6-ethoxy-indole-3-carbonitrile

Produkt 1

HCID 49772271N-[4-(3-cyano-1-cyclobutyl-6-ethoxy-indol-2-yl)phenyl]morpholine-4-carboxamideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2-(4-aminophenyl)-1-cyclobutyl-6-ethoxy-1H-indole-3-carbonitrile (40 mg, 0.12 mmol), 4-nitrophenyl chloroformate (60 mg, 0.30 mmol), CH2Cl2 (400 μL), and pyridine (25 μL, 0.31 mmol) are stirred at room temperature for 1 hour. Morpholine (60 μL, 0.70 mmol) is added. After stirring at room temperature for an additional 30 minutes, the reaction mixture is diluted in CH2Cl2 and is washed with dilute aqueous NaOH to remove the yellow nitrophenol byproduct. The organic layer is dried and concentrated. Purification by silica gel chromatography (CH2Cl2/EtOAc, 7/3) yields morpholine-4-carboxylic acid [4-(3-cyano-1-cyclobutyl-6-ethoxy-1H-indol-2-yl)-phenyl]-amide (53 mg, 100%) as a white solid.

Aufarbeitung

  1. washis washed with dilute aqueous NaOH
  2. customto remove the yellow nitrophenol byproduct
  3. customThe organic layer is dried
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (CH2Cl2/EtOAc, 7/3)

Quellen und Nachweise

ORD-Eintrag
ord-fab1d3f0061e4b6a8ec36148d11d4e48
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772271B2

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