Acryloyl chloride → N-methyl-N-(6-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)pyridin-2-yl)acrylamide

HRID 404793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 404793
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([NH:9][C:10]2[CH:15]=[C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:19][CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:5][CH:4]=1.[C:30](Cl)(=[O:33])[CH:31]=[CH2:32]>CN1C(=O)CCC1.ClCCl>[CH3:1][N:2]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([NH:9][C:10]2[CH:15]=[C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:19][CH:18]=3)[N:13]=[CH:12][N:11]=2)[N:8]=1)[C:30](=[O:33])[CH:31]=[CH2:32]

Komponenten

5

Edukt 2

HCID 13140Acryloyl chlorideHCID 57708271N4-(6-(methylamino)pyridine-2-yl)-N6-(4-phenoxyphenyl)pyrimidine-4,6-diamine

Produkt 1

HCID 42601657N-methyl-N-(6-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)pyridin-2-yl)acrylamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

To a solution of N4-(6-(methylamino)pyridine-2-yl)-N6-(4-phenoxyphenyl)pyrimidine-4,6-diamine (0.07 g, 0.18 mmol) in NMP (1 mL) was added acryloyl chloride (0.032 g, 0.36 mmol) at 0° C. and the reaction mixture was stirred at rt for 1 h. The reaction mixture was diluted with dichloromethane (2 mL), was washed with NaHCO3 (1 mL), water (1 mL), and brine (1 mL). The dichloromethane solution was dried over Na2SO4 and was concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, 60-120, chloroform/methanol, 9/1) to give N-methyl-N-(6-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)pyridin-2-yl)acrylamide (I-78) as a yellow solid. 1H NMR (DMSO-d6) δ ppm: 3.22 (s, 3H), 5.60 (dd, J=2.56 & 9.76 Hz, 1H), 6.12-6.16 (m, 2H), 6.79 (d, J=7.56 Hz, 1H), 6.96 (d, J=8.64 Hz, 5H), 7.09 (t, J=7.32 Hz, 1H), 7.23 (s, 1H), 7.33-7.37 (m, 4H), 7.45 (d, J=8.2 Hz, 2H), 7.32 (t, J=7.8 Hz, 1H), 8.24 (s, 1H); LCMS: m/e 439.3 (M+1).

Aufarbeitung

  1. washwas washed with NaHCO3 (1 mL), water (1 mL), and brine (1 mL)
  2. dry with materialThe dichloromethane solution was dried over Na2SO4
  3. concentrationwas concentrated under reduced pressure
  4. customThe residue was purified by column chromatography (SiO2, 60-120, chloroform/methanol, 9/1)

Quellen und Nachweise

ORD-Eintrag
ord-19bf25ca4cd74fcaaaa7ffe4e78b0fbb
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748606B2

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