Acetone → (7R,8R,9R)-8-Hydroxy-7-methoxy-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

HRID 723388노트

반응식

HRID 723388 반응식
[OH:1][C@H:2]1[C:11]2[CH:10]=[CH:9][N:8]3[CH:12]=[C:13]([CH3:15])[N:14]=[C:7]3[C:6]=2[NH:5][C@H:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@H:3]1[OH:22].[C:23]1(C)C=CC(S(O)(=O)=O)=CC=1.CC(C)=O>COC(OC)(C)C>[OH:22][C@H:3]1[C@H:2]([O:1][CH3:23])[C:11]2[CH:10]=[CH:9][N:8]3[CH:12]=[C:13]([CH3:15])[N:14]=[C:7]3[C:6]=2[NH:5][C@@H:4]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

5

반응물 3

HCID 180AcetoneHCID 6101p-Toluenesulfonic acidHCID 69230549(7S,8R,9R)-7,8-Dihydroxy-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

생성물 1

HCID 69105665(7R,8R,9R)-8-Hydroxy-7-methoxy-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

시약·촉매·용매 1

HCID 64952,2-Dimethoxypropane용매

반응 조건

온도
25 °C

실험 절차

To a suspension of 0.62 g (2.10 mmol) (7S,8R,9R)-7,8-dihydroxy-2-methyl-9-phenyl-7.8.9.10-tetrahydroimidazo[1.2-h][1.7]naphthyridine in dimethoxypropane is added 0.51 g (26.2 mmol) p-toluenesulphonic acid and acetone (4.0 ml). The mixture is stirred for 6 h at 60° C. and 96 h at 25° C. The reaction is quenched by adding of saturated aqueous sodium hydrogen carbonate solution. Subsequently the mixture is extracted twice with dichloromethane. The combined organic layers are washed with brine, dried over sodium sulphate and evaporated in vacuo. The crude product is purified by column chromatography (dichloromethane/methanol: 100/3) to give 0.12 g (0.34 mmol/16%) of the title compound as an amorphous solid. 1H-NMR (200 MHz, [D6] DMSO): δ=2.29 (s, 3H), 3.25 (s, 3 H), 4.05 (q, 1H), 4.32 (d, 1H), 4.47 (dd, 1H), 6.61 (d, 1H), 7.19–7.46 (m, 5H), 7.54 (s, 1H), 7.72 (d, 1 H).

후처리

  1. customThe reaction is quenched
  2. additionby adding of saturated aqueous sodium hydrogen carbonate solution
  3. extractionSubsequently the mixture is extracted twice with dichloromethane
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo
  7. customThe crude product is purified by column chromatography (dichloromethane/methanol: 100/3)

출처 및 근거

ORD 기록
ord-ed02dabe22b142d3ae02cf97fa858741
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141567B2

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