Trifluoroacetic acid → Ethyl 1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo(3,4-c)pyridine-3-carboxylate

HRID 860829노트

반응식

HRID 860829 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:14]2[C:9](N3CCOCC3)([C:10](=[O:15])[NH:11][CH2:12][CH2:13]2)[N:8]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[N:7]=1)=[O:5])[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[CH2:13][CH2:12][NH:11][C:10](=[O:15])[C:9]=2[N:8]([C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)[N:7]=1)=[O:5])[CH3:2]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 208161461-(4-Methoxy-phenyl)-7a-morpholin-4-yl-7-oxo-3a,4,5,6,7,7a-hexahydro-1H-pyrazolo[3,4-c]pyridin-3-carboxylic acid ethyl ester

생성물 1

HCID 22240468Ethyl 1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo(3,4-c)pyridine-3-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
25 °C

실험 절차

Method B. A solution of 1-(4-methoxy-phenyl)-7a-morpholin-4-yl-7-oxo-3a,4,5,6,7,7a-hexahydro-1H-pyrazolo[3,4-c]pyridin-3-carboxylic acid ethyl ester (51, 402 mg, 1.0 mmol) in methylene chloride (CH2Cl2, 4 mL) was treated with trifluoroacetic acid (TFA, 1.0 mL) at 25° C., and the resulting reaction mixture was stirred at 25° C. for an additional 30 min. When HPLC and TLC showed the reaction was complete, the solvents were removed in vacuo. The residue was directly purified by flash column chromatography (SiO2, 5–30% EtOAc/hexane gradient elution) to afford the desired elimination product (50, 299 mg, 315 mg theoretical, 95%) as a pale-yellow oil, which solidified upon standing at room temperature in vacuo. This material was found to be identical with the product obtained from method A in every comparable aspect.

후처리

  1. customthe resulting reaction mixture
  2. customthe solvents were removed in vacuo
  3. customThe residue was directly purified by flash column chromatography (SiO2, 5–30% EtOAc/hexane gradient elution)
  4. customto afford the desired elimination product (50, 299 mg, 315 mg theoretical, 95%) as a pale-yellow oil, which
  5. customupon standing at room temperature in vacuo

출처 및 근거

ORD 기록
ord-175ad3f1094f46d29cc66e4971336702
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153960B2

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