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N-(2-((1-(4-chlorobenzyl)piperidin-4-yl)methylamino)-2-oxoethyl)-2-amino-5-(trifluoromethyl)benzamide → 4-[[N-(2-amino-5-trifluoromethylbenzoyl)glycyl]aminomethyl]piperidine

HRID 279322
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인쇄 미리보기

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HRID 279322 반응식
ClC1C=CC(C[N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][C:15](=[O:31])[CH2:16][NH:17][C:18](=[O:30])[C:19]3[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:20]=3[NH2:29])[CH2:9][CH2:8]2)=CC=1>C(O)=O.CO.[OH-].[OH-].[Pd+2]>[NH2:29][C:20]1[CH:21]=[CH:22][C:23]([C:25]([F:28])([F:26])[F:27])=[CH:24][C:19]=1[C:18]([NH:17][CH2:16][C:15]([NH:14][CH2:13][CH:10]1[CH2:9][CH2:8][NH:7][CH2:12][CH2:11]1)=[O:31])=[O:30]
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참가 물질

4

반응물 1

HCID 9934977N-(2-((1-(4-chlorobenzyl)piperidin-4-yl)methylamino)-2-oxoethyl)-2-amino-5-(trifluoromethyl)benzamide

생성물 1

HCID 184262274-[[N-(2-amino-5-trifluoromethylbenzoyl)glycyl]aminomethyl]piperidine수율 86%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 18963719Formic acid methanol용매

반응 조건

온도
50 °C

실험 절차

A suspension of 1-(4-chlorobenzyl)-4-[{(N-(2-amino-5-trifluoromethylbenzoyl)glycyl)amino}methyl]piperidine (447 mg, 0.93 mmol) and Pd(OH)2 (60 mg, 0.23 mmol) in 5% HCO2H/methanol (10 mL) was stirred at 50° C. for 14 h. The Pd catalyst was filtered off through Celite, and the filtrate was concentrated. To the residue was added 1N aqueous NaOH solution (15 mL) and the mixture was extracted with ethyl acetate (30 mL×3). The combined extracts were dried over anhydrous sodium sulfate, filtered, and concentrated. Column chromatography (SiO2, AcOEt/MeOH/Et3N=70/25/5) gave 4-[{(N-(2-amino-5-trifluoromethylbenzoyl)glycyl)amino}methyl]piperidine (284 mg, 86%): ESI/MS m/e 359.0 (M++H, C16H21F3N4O2).

후처리

  1. filtrationThe Pd catalyst was filtered off through Celite
  2. concentrationthe filtrate was concentrated
  3. additionTo the residue was added 1N aqueous NaOH solution (15 mL)
  4. extractionthe mixture was extracted with ethyl acetate (30 mL×3)
  5. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-df42a15e4149489e81981255e6c06457
출처 데이터셋
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06362177B1

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