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 530354ノート

反応式

HRID 530354 の反応式
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]

参加物

6

反応物 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

生成物 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)ethanesulfonamide収率 29%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-fdf8f890545741d3aa3fc4050e2a8555
出典データセット
uspto-grants-2016_05
特許番号
US09353081B2

反応ノート

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