Acryloyl chloride → N-(6-(6-(3-methoxyphenoxy)pyrimidin-4-ylamino)pyridine-2-yl)acrylamide

HRID 929870

Reaktionsgleichung

Reaktionsgleichung von HRID 929870
[O:1]([C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[N:15]=2)[CH:8]=1)[CH3:2].[C:24](Cl)(=[O:27])[CH:25]=[CH2:26]>C1COCC1.CN1C(=O)CCC1>[CH3:2][O:1][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]2[N:15]=[C:16]([NH:20][C:24](=[O:27])[CH:25]=[CH2:26])[CH:17]=[CH:18][CH:19]=2)[CH:8]=1

Komponenten

4

Edukt 2

HCID 13140Acryloyl chlorideHCID 57708231N2-(6-(3-methoxylphenoxy)pyrimidin-4-yl)pyridine-2,6-diamine

Produkt 1

HCID 42601817N-(6-(6-(3-methoxyphenoxy)pyrimidin-4-ylamino)pyridine-2-yl)acrylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22156051tetrahydrofuran N-methylpyrrolidinoneLösungsmittel

Versuchsvorschrift

To a stirred solution of N2-(6-(3-methoxylphenoxy)pyrimidin-4-yl)pyridine-2,6-diamine (100 mg, 0.323 mmol) in THF/NMP (1 mL/0.5 mL) was added acryloyl chloride (0.029 g, 0.3 mmol) under N2 atmosphere at −10° C. The stirring was continued at the same temperature for 2 h and the reaction mixture was concentrated under reduced pressure to give a residue that was further purified by column chromatography (SiO2, 60-120, chloroform/methanol) to give N-(6-(6-(3-methoxyphenoxy)pyrimidin-4-ylamino)pyridine-2-yl)acrylamide (I-90) as a pale yellow solid. 1H NMR (DMSO-d6) δ ppm: 3.75 (s, 3H), 5.79 (dd, J=1.8 & 10.08 Hz, 1H), 6.30 (dd, J=1.8 & 16.96 Hz, 1H), 6.65 (dd, J=10.12 & 16.96 Hz, 1H), 6.74-6.76 (m, 2H), 6.82 (td, J=1.52 & 9.24 Hz, 1H), 7.04 (d, J=7.92 Hz, 1H), 7.33 (t, J=8.28 Hz, 1H), 7.70 (t, J=7.96 Hz, 1H), 7.76 (d, J=8 Hz, 1H), 7.90 (s, 1H), 8.34 (s, 1H), 10.20 (s, 1H), 10.48 (s, 1H); LCMS: m/e 364 (M+1).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customto give a residue that
  3. customwas further purified by column chromatography (SiO2, 60-120, chloroform/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-f6bccf183e3b418b8181cbb800b19778
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296704B2

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