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4-[1-(5-chlorothiophen-2-ylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-piperidine-1-carboxylic acid tert-butyl ester → 1-(5-chlorothiophen-2-ylmethyl)3-piperidin-4-yl-1H-pyrrolo[2,3-b]pyridine

HRID 1437178
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HRID 1437178 반응식
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:23][C:24]3[S:25][C:26]([Cl:29])=[CH:27][CH:28]=3)[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[Cl:29][C:26]1[S:25][C:24]([CH2:23][N:16]2[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:22]3[C:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[CH:15]2)=[CH:28][CH:27]=1
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참가 물질

4

반응물 1

HCID 688942864-[1-(5-chlorothiophen-2-ylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 179729751-(5-chlorothiophen-2-ylmethyl)3-piperidin-4-yl-1H-pyrrolo[2,3-b]pyridine수율 127.8%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 6422Trifluoroacetic acid용매

실험 절차

Over a solution of 2.86 g (6.6 mmol) of 4-[1-(5-chlorothiophen-2-ylmethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-piperidine-1-carboxylic acid tert-butyl ester in 20 ml of dichloromethane, 5.1 ml of trifluoroacetic acid were added. After 1 hour at room temperature, the solvent was removed under reduced pressure. The crude mixture was dissolved in ethyl acetate and washed with saturated solution of potassium carbonate and brine. The organic phase was dried over magnesium sulphate, filtered and removed under reduced pressure affording 2.8 g of a crude mixture which was pure enough for the next synthetic step.

후처리

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe crude mixture was dissolved in ethyl acetate
  3. washwashed with saturated solution of potassium carbonate and brine
  4. dry with materialThe organic phase was dried over magnesium sulphate
  5. filtrationfiltered
  6. customremoved under reduced pressure

출처 및 근거

ORD 기록
ord-cc94ff028c0c463e8785f153e81140ef
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07622480B2

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