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 82860ノート

反応式

HRID 82860 の反応式
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

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-0c522fa8dbc34f79bc0b37a6eee55150
出典データセット
uspto-grants-2014_09
特許番号
US08846741B2

反応ノート

読み込み中…