Sulfuric Acid → (7R,8R,9R)-2,3-dimethyl-8-hydroxy-7-(2-methylthioethyloxy)-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

HRID 1934369노트

반응식

HRID 1934369 반응식
[OH:1][C@@H:2]1[C:11]2[CH:10]=[CH:9][N:8]3[C:12]([CH3:16])=[C:13]([CH3:15])[N:14]=[C:7]3[C:6]=2[NH:5][C@H:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:3]1[OH:23].S(=O)(=O)(O)O.[CH3:29][S:30][CH2:31][CH2:32]O.[OH-].[Na+]>O1CCOCC1.CN(C)C=O>[CH3:15][C:13]1[N:14]=[C:7]2[C:6]3[NH:5][C@H:4]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[C@@H:3]([OH:23])[C@H:2]([O:1][CH2:32][CH2:31][S:30][CH3:29])[C:11]=3[CH:10]=[CH:9][N:8]2[C:12]=1[CH3:16]

참가 물질

7

반응물 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 789252-(Methylthio)ethanolHCID 10215014(7R,8R,9R)-2,3-dimethyl-7,8-dihydroxy-9-phenyl-7,8,9,10-tetrahydro-imidazo[1,2-h][1,7]naphthyridine

생성물 1

HCID 9929931(7R,8R,9R)-2,3-dimethyl-8-hydroxy-7-(2-methylthioethyloxy)-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 312751,4-Dioxane용매

실험 절차

1 g of (7R,8R,9R)-7,8-dihydroxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine, dissolved in 30 ml of dioxane and 5 ml of dimethyl-formamide, is admixed with 0.63 g of concentrated sulfuric acid and 1 g of 2-methylmercaptoethanol. The mixture is stirred at RT for 3 h, poured into ice-water (200 ml), adjusted to pH 8 using 2 N aqueous sodium hydroxide solution and extracted three times with methylene chloride. The solvent is stripped off under reduced pressure and the oily residue that remains is purified on silica gel (mobile phase: diethyl ether). This gives 80 mg of the title compound of m.p. 118-9° C. (diisopropyl ether).

후처리

  1. extractionextracted three times with methylene chloride
  2. customthe oily residue that remains is purified on silica gel (mobile phase: diethyl ether)

출처 및 근거

ORD 기록
ord-e085237b4e2d4c689ec06e95e47285e4
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06384048B1

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