Methanol → cis-N-(2-{[7-[3-Azabicyclo[3.1.0]hex-3-yl]-8-(2-fluorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}ethyl)-1-methyl-1H-imidazole-4-sulfonamide

HRID 82860노트

반응식

HRID 82860 반응식
O=[C:2]1[N:7]([C@H:8]2[C@@H:17]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[C:16]3[CH:15]=[C:14]([O:26][CH2:27][CH2:28][NH:29][S:30]([C:33]4[N:34]=[CH:35][N:36]([CH3:38])[CH:37]=4)(=[O:32])=[O:31])[CH:13]=[CH:12][C:11]=3[CH2:10][CH2:9]2)[C:6](=O)[CH:5]2[CH:3]1[CH2:4]2.CO>O1CCCC1.ClCCl>[CH:5]12[CH2:4][CH:3]1[CH2:2][N:7]([C@H:8]1[C@@H:17]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[C:16]3[CH:15]=[C:14]([O:26][CH2:27][CH2:28][NH:29][S:30]([C:33]4[N:34]=[CH:35][N:36]([CH3:38])[CH:37]=4)(=[O:32])=[O:31])[CH:13]=[CH:12][C:11]=3[CH2:10][CH2:9]1)[CH2:6]2

참가 물질

5

반응물 2

HCID 887MethanolHCID 86685678cis-N-(2-{[7-(2,4-Dioxo-3-azabicyclo[3.1.0]hex-3-yl)-8-(2-fluorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}ethyl)-1-methyl-1H-imidazole-4-sulfonamide

생성물 1

HCID 86685679cis-N-(2-{[7-[3-Azabicyclo[3.1.0]hex-3-yl]-8-(2-fluorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}ethyl)-1-methyl-1H-imidazole-4-sulfonamide

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

cis-N-(2-{[7-(2,4-Dioxo-3-azabicyclo[3.1.0]hex-3-yl)-8-(2-fluorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}ethyl)-1-methyl-1H-imidazole-4-sulfonamide (38 mg, 0.069 mmol) was dissolved in tetrahydrofuran (2 mL) and borane tetrahydrofuran complex was added (1 N, 0.4 mL, 0.4 mmol). The reaction mixture was heated to 50° C. for 3.5 h. After cooling to room temperature methanol (0.2 mL) was added dropwise and stirring was continued for 30 min. The reaction mixture was diluted with dichloromethane, washed with saturated sodium chloride solution and dried (magnesium sulfate). The solvent was evaporated in vacuo and the crude product was purified by flash chromatography (silica, dichloromethane/methanol). Yield: 4 mg (7.6 μmol, 11%, colorless oil).

후처리

  1. additionborane tetrahydrofuran complex was added (1 N, 0.4 mL, 0.4 mmol)
  2. additionwas added dropwise
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried (magnesium sulfate)
  5. customThe solvent was evaporated in vacuo
  6. customthe crude product was purified by flash chromatography (silica, dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-0c522fa8dbc34f79bc0b37a6eee55150
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846741B2

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