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 1774645노트

반응식

HRID 1774645 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-7dde1bb3de2c46bf9a77bdafa2c58993
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260415B2

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