1521788-97-5 → HCID 86706976, Verbindung

HRID 1750305

Reaktionsgleichung

Reaktionsgleichung von HRID 1750305
[CH3:1][C:2]1[CH:6]=[C:5]([CH:7]2[O:12][CH2:11][CH2:10][NH:9][CH2:8]2)[O:4][N:3]=1.Cl[C:14]1[C:15]2[C:22]([C:23]3[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=3)[C:26]#[N:27])=[CH:21][NH:20][C:16]=2[N:17]=[CH:18][N:19]=1>C(O)CCC>[CH3:1][C:2]1[CH:6]=[C:5]([CH:7]2[O:12][CH2:11][CH2:10][N:9]([C:14]3[C:15]4[C:22]([C:23]5[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=5)[C:26]#[N:27])=[CH:21][NH:20][C:16]=4[N:17]=[CH:18][N:19]=3)[CH2:8]2)[O:4][N:3]=1

Komponenten

4

Edukt 2

HCID 566104531521788-97-5HCID 867069533-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile

Produkt 1

HCID 86706976HCID 86706976, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a solution of 2-(3-methyl-1,2-oxazol-5-yl)morpholine (C38) (20 mg, 0.12 mmol) in n-butanol (7 mL) was added 3-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)benzonitrile (C14) (36.2 mg, 0.142 mol), and the reaction mixture was placed in a sealed tube and heated at 150° C. in a microwave reactor for 2 hours. After removal of solvent, the residue was purified by preparative reversed phase high-performance liquid chromatography (Column: YMC-Actus Triart C18, 5 μm; Mobile phase A: water containing 0.225% formic acid; Mobile phase B: acetonitrile; Gradient: 33% to 53% B) to afford the product as a white solid. Yield: 0.78 mg, 2.0 μmol, 2%. LCMS m/z 387.0[M+H+]. 1H NMR (400 MHz, DMSO-d6), characteristic peaks: δ 12.45 (br s, 1H), 8.45 (s, 1H), 8.00-8.03 (m, 1H), 7.85 (br d, J=8 Hz, 1H), 7.76 (br d, J=8 Hz, 1H), 7.72 (d, J=2.8 Hz, 1H), 7.66 (dd, J=8, 8 Hz, 1H), 6.25 (s, 1H), 4.58-4.63 (m, 1H), 3.71-3.83 (m, 2H), 3.01-3.09 (m, 1H), 2.88-2.97 (m, 1H), 2.20 (s, 3H).

Aufarbeitung

  1. customthe reaction mixture was placed in a sealed tube
  2. customAfter removal of solvent
  3. customthe residue was purified by preparative reversed phase high-performance liquid chromatography (Column: YMC-Actus Triart C18, 5 μm; Mobile phase A: water containing 0.225% formic acid; Mobile phase B: acetonitrile; Gradient: 33% to 53% B)

Quellen und Nachweise

ORD-Eintrag
ord-7de9ffbd51774e238bc70cf8dd50927b
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156845B2

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