Cyclopentylacetyl chloride → 2-Cyclopentyl-N-(2,6-difluoro-4-morpholin-4-yl-phenyl)-acetamide

HRID 1158698

Reaktionsgleichung

Reaktionsgleichung von HRID 1158698
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[C:4]([F:14])[C:3]=1[NH2:15].[CH:16]1([CH2:21][C:22](Cl)=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17]1>C(#N)C>[CH:16]1([CH2:21][C:22]([NH:15][C:3]2[C:2]([F:1])=[CH:7][C:6]([N:8]3[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)=[CH:5][C:4]=2[F:14])=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17]1

Komponenten

4

Edukt 2

HCID 3485182Cyclopentylacetyl chlorideHCID 592443842,6-Difluoro-4-morpholin-4-yl-phenylamine

Produkt 1

HCID 116022552-Cyclopentyl-N-(2,6-difluoro-4-morpholin-4-yl-phenyl)-acetamideAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

2,6-Difluoro-4-morpholin-4-yl-phenylamine (0.20 g) and cyclopentylacetyl chloride (149 μL) were dissolved in acetonitrile (4 mL) and heated to 150° C. for 10 minutes in a sealed microwave process vial. The reaction mixture was concentrated in vacuo and purified by flash chromatography to furnish 228 mg (75%) of the title compound as a white solid. LC-MS (m/z) 325 (MIT); tR=2.61, (UV, ELSD) 99%, 99%. 1H NMR (500 MHz, DMSO-d6): 1.19 (m, 2H), 1.51 (m, 2H), 1.60 (m, 2H), 1.74 (m, 2H), 2.19 (m, 1H), 2.26 (d, 2H), 3.14 (m, 4H), 3.70 (m, 4H), 6.68 (d, 2H), 9.20 (s, 1H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-93286c105e904b899605a3bda9d7b0c8
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812023B2

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