Water → N-(2-(5-(1-Methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-3,4-dihydro-1,7-naphthyridin-1(2H)-yl)ethyl)ethanesulfonamide

HRID 530354노트

반응식

HRID 530354 반응식
Cl.[NH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[C:10]([C:15]3[CH:16]=[C:17]4[C:22](=[CH:23][CH:24]=3)[N:21]([CH3:25])[C:20](=[O:26])[CH2:19][CH2:18]4)[CH:11]=[N:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1.C(N(CC)CC)C.[CH2:34]([S:36](Cl)(=[O:38])=[O:37])[CH3:35].O>C(Cl)Cl>[CH3:25][N:21]1[C:22]2[C:17](=[CH:16][C:15]([C:10]3[CH:11]=[N:12][CH:13]=[C:14]4[C:9]=3[CH2:8][CH2:7][CH2:6][N:5]4[CH2:4][CH2:3][NH:2][S:36]([CH2:34][CH3:35])(=[O:38])=[O:37])=[CH:24][CH:23]=2)[CH2:18][CH2:19][C:20]1=[O:26]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 715364856-[1-(2-Amino-ethyl)-1,2,3,4-tetrahydro-[1,7]naphthyridin-5-yl]-1-methyl-3,4-dihydro-1H-quinolin-2-one hydrochloride

생성물 1

HCID 71536488N-(2-(5-(1-Methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)-3,4-dihydro-1,7-naphthyridin-1(2H)-yl)ethyl)ethanesulfonamide수율 29%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 6-[1-(2-amino-ethyl)-1,2,3,4-tetrahydro-[1,7]naphthyridin-5-yl]-1-methyl-3,4-dihydro-1H-quinolin-2-one hydrochloride (example 12, 0.03 g, 0.081 mmol) in DCM (1 mL) were added triethylamine (0.020 g, 0.201 mmol) and ethanesulfonylchloride (0.011 g, 0.089 mmol) and the reaction mixture was stirred at room temperature for 1.5 h. The mixture was diluted with DCM, poured into H2O (5 mL) and extracted with DCM (2×10 mL). Combined organics were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 5% MeOH-DCM gradient to give the title compound (0.01 g, 29%) as a yellow oil. MS: 429.2 (M+H+).

후처리

  1. extractionextracted with DCM (2×10 mL)
  2. dry with materialCombined organics were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was purified by silica gel flash chromatography
  6. washeluting with a 0 to 5% MeOH-DCM gradient

출처 및 근거

ORD 기록
ord-fdf8f890545741d3aa3fc4050e2a8555
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353081B2

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