Acetic Acid → 4-Hydroxy-7-{1-(tert-butoxycarbonyl)-5-[4-(2-hydroxyethyl)piperazin-1-ylmethyl]indol-2-yl}isoindolinone

HRID 21097

반응식

HRID 21097 반응식
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH:20]=O)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29].[OH:30][CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>C(#N)C>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][N:36]2[CH2:37][CH2:38][N:33]([CH2:32][CH2:31][OH:30])[CH2:34][CH2:35]2)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29]

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 76771-(2-Hydroxyethyl)piperazineHCID 5049666Sodium triacetoxyborohydride3회HCID 866282304-Hydroxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

생성물 1

HCID 684908204-Hydroxy-7-{1-(tert-butoxycarbonyl)-5-[4-(2-hydroxyethyl)piperazin-1-ylmethyl]indol-2-yl}isoindolinone수율 79.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

4-Hydroxy-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (140 mg, 0.357 mmol) was dissolved in acetonitrile (7 mL), and the solution was added with 1-(2-hydroxyethyl)piperazine (186 mg, 1.43 mmol), acetic acid (0.409 mL, 7.14 mmol) and sodium triacetoxyborohydride (151 mg, 0.714 mmol), followed by stirring at room temperature for 1.3 hours. The mixture was added with sodium triacetoxyborohydride (151 mg, 0.714 mmol) and further stirred for 3.8 hours. Further, the mixture was added with sodium triacetoxyborohydride (76.0 mg, 0.357 mmol) and stirred for 0.6 hours. The reaction mixture was added with 1 mol/L hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 4-hydroxy-7-{1-(tert-butoxycarbonyl)-5-[4-(2-hydroxyethyl)piperazin-1-ylmethyl]indol-2-yl}isoindolinone (143 mg, yield 79%).

후처리

  1. stirringfurther stirred for 3.8 hours
  2. stirringstirred for 0.6 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium carbonate solution and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-36e7e9b1731342d4b582ad326c52be7f
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

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