Morpholine → PF-06447475

HRID 1750274

Reaktionsgleichung

Reaktionsgleichung von HRID 1750274
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.Cl[C:17]1[C:18]2[C:25]([C:26]3[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=3)[C:29]#[N:30])=[CH:24][NH:23][C:19]=2[N:20]=[CH:21][N:22]=1>C(O)CCC>[N:1]1([C:17]2[C:18]3[C:25]([C:26]4[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=4)[C:29]#[N:30])=[CH:24][NH:23][C:19]=3[N:20]=[CH:21][N:22]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 86706953HCID 86706953, Verbindung

Produkt 1

HCID 72706840PF-06447475

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

Morpholine (871 mg, 10 mmol) and N,N-diisopropylethylamine (2.6 g, 20 mmol) were added to a solution of 3-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile (C14) (2.5 g, 9.8 mmol) in n-butanol (100 mL), and the reaction mixture was heated at reflux for 3 hours. Solvents were removed in vacuo and the residue was purified using chromatography on silica gel (Eluent: 1:1 ethyl acetate/petroleum ether). Subsequent recrystallization from ethyl acetate and tert-butyl methyl ether afforded the product as a white solid. Yield: 770 mg, 2.52 mmol, 26%. LCMS m/z 306.0 [M+H+]. 1H NMR (400 MHz, DMSO-d6) δ 12.34 (br s, 1H), 8.41 (s, 1H), 7.99-8.02 (m, 1H), 7.89 (br d, J=8 Hz, 1H), 7.76 (br d, J=7.5 Hz, 1H), 7.71 (s, 1H), 7.68 (dd, J=7.8, 7.8 Hz, 1H), 3.44-3.50 (m, 4H), 3.11-3.17 (m, 4H).

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. customSolvents were removed in vacuo
  4. customthe residue was purified
  5. customSubsequent recrystallization from ethyl acetate and tert-butyl methyl ether

Quellen und Nachweise

ORD-Eintrag
ord-3e4bfd929c1444d18be2db7165ad47f4
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156845B2

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