N-(1-benzyl-6-(2-(1-methyl-1H-imidazole-4-sulfonamido)ethoxy)-2,3-dihydro-1H-inden-2-yl)-3-chloro-2,2-dimethylpropanamide → N-(2-(3-benzyl-2-(3-chloro-2,2-dimethylpropylamino)-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide

HRID 82894

反応式

HRID 82894 の反応式
[CH2:1]([CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:18][CH2:19][NH:20][S:21]([C:24]3[N:25]=[CH:26][N:27]([CH3:29])[CH:28]=3)(=[O:23])=[O:22])[CH:15]=2)[CH2:10][CH:9]1[NH:30][C:31](=O)[C:32]([CH3:36])([CH3:35])[CH2:33][Cl:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1>[CH2:1]([CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:18][CH2:19][NH:20][S:21]([C:24]3[N:25]=[CH:26][N:27]([CH3:29])[CH:28]=3)(=[O:23])=[O:22])[CH:15]=2)[CH2:10][CH:9]1[NH:30][CH2:31][C:32]([CH3:36])([CH3:35])[CH2:33][Cl:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

3

反応物 1

HCID 66740419N-(1-benzyl-6-(2-(1-methyl-1H-imidazole-4-sulfonamido)ethoxy)-2,3-dihydro-1H-inden-2-yl)-3-chloro-2,2-dimethylpropanamide

生成物 1

HCID 66741593N-(2-(3-benzyl-2-(3-chloro-2,2-dimethylpropylamino)-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To a solution of N-(1-benzyl-6-(2-(1-methyl-1H-imidazole-4-sulfonamido)ethoxy)-2,3-dihydro-1H-inden-2-yl)-3-chloro-2,2-dimethylpropanamide (51.8 mg, 0.095 mmol) in dry tetrahydrofuran (1 ml) was added 2M borane dimethyl complex (0.143 ml, 0.285 mmol) and stirred at 60° C. for 6 h and at room temperature over night. Quenched by dropwise addition of 0.5N hydrochloric acid and refluxed for an other 2 h, the solution was saponified with sodium hydroxide and extracted three times with dichloromethane, dried, filtered and evaporated to obtain the crude product (m=53 mg) as a yellow oil that was purified by flash silica gel chromatography on 4 g SiO2-cartridge using 5% methanol in dichloromethane to afford the titled compound N-(2-(3-benzyl-2-(3-chloro-2,2-dimethylpropylamino)-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide as a pale yellow oil. m=17.7 mg (35%)

後処理

  1. customQuenched by dropwise addition of 0.5N hydrochloric acid
  2. temperaturerefluxed for an other 2 h
  3. extractionextracted three times with dichloromethane
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customto obtain the crude product (m=53 mg) as a yellow oil that
  8. customwas purified by flash silica gel chromatography on 4 g SiO2-cartridge

出典と根拠

ORDレコード
ord-143a082659a045ec979e52478a05df80
出典データセット
uspto-grants-2014_09
特許番号
US08846743B2

関連ノート

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