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 530354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530354
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]

Komponenten

6

Edukt 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

Produkt 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)ethanesulfonamideAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-fdf8f890545741d3aa3fc4050e2a8555
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353081B2

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