Acryloyl chloride → (S)-N-(1-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-yloxy)propan-2-yl)acrylamide

HRID 1774645Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1774645
Cl.[NH2:2][C@@H:3]([CH3:22])[CH2:4][O:5][C:6]1[N:11]=[C:10]([NH:12][C:13]2[C:14](=[O:21])[N:15]([CH3:20])[CH:16]=[C:17]([Br:19])[CH:18]=2)[CH:9]=[CH:8][CH:7]=1.[C:23](Cl)(=[O:26])[CH:24]=[CH2:25]>C(Cl)Cl>[Br:19][C:17]1[CH:18]=[C:13]([NH:12][C:10]2[N:11]=[C:6]([O:5][CH2:4][C@@H:3]([NH:2][C:23](=[O:26])[CH:24]=[CH2:25])[CH3:22])[CH:7]=[CH:8][CH:9]=2)[C:14](=[O:21])[N:15]([CH3:20])[CH:16]=1

Komponenten

4

Edukt 2

HCID 13140Acryloyl chlorideHCID 118117014(S)-3-(6-(2-aminopropoxyl)pyridin-2-ylamino)-5-bromo-1-methylpyridin-2(1H)-one hydrochloride

Produkt 1

HCID 118116485(S)-N-(1-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-2-yloxy)propan-2-yl)acrylamideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To an ice-cooled mixture of 107c (390 mg, 1.0 mmol) and TEA (0.53 ml, 3.0 mmol) in DCM (20 mL) was added acryloyl chloride (0.23 ml, 2.0 mmol) dropwise. The reaction mixture was stirred at rt for 2 h and quenched with water. The organic layer was separated, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography (DCM/MeOH=10/1) to give 107d (284 mg, 70%) as brown solid. MS-ESI: [M+H]+ 409.0

Aufarbeitung

  1. customquenched with water
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (DCM/MeOH=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-7dde1bb3de2c46bf9a77bdafa2c58993
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09260415B2

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