Acetic Acid → 4-Chloro-7-{1-(tert-butoxycarbonyl)-5-[(aminocarbonylmethyl)aminomethyl]indol-2-yl}isoindolinone

HRID 21023

반응식

HRID 21023 반응식
[Cl: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].Cl.[NH2:31][CH2:32][C:33]([NH2:35])=[O:34].C(N(CC)CC)C.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>C(#N)C.C(OCC)(=O)C>[Cl: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][NH:31][CH2:32][C:33]([NH2:35])=[O:34])=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29]

참가 물질

9

반응물 6

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 2723639Glycinamide hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 866282274-Chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

생성물 1

HCID 684913184-Chloro-7-{1-(tert-butoxycarbonyl)-5-[(aminocarbonylmethyl)aminomethyl]indol-2-yl}isoindolinone수율 120.6%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

In a similar manner to Step 2 of Example 6, 4-chloro-7-[1-(tert.-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (30.0 mg, 0.0730 mmol) was dissolved in acetonitrile (2 mL), and the solution was treated with glycineamide hydrochloride (96 mg, 0.87 mmol), triethylamine (0.243 mL, 1.74 mmol), acetic acid (0.252 mL, 4.40 mmol) and sodium triacetoxyborohydride (231 mg, 1.09 mmol). The reaction mixture was added with 1 mol/L hydrochloric acid and ethyl acetate, followed by extracting with 1 mol/L hydrochloric acid. The aqueous layer was added with sodium carbonate to adjust the pH to 9. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 4-chloro-7-{1-(tert-butoxycarbonyl)-5-[(aminocarbonylmethyl)aminomethyl]indol-2-yl}isoindolinone (41.3 mg).

후처리

  1. extractionby extracting with 1 mol/L hydrochloric acid
  2. additionThe aqueous layer was added with sodium carbonate
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-438793ff082649f88c1c2e9a199250a3
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

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