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

HRID 860829ノート

反応式

HRID 860829 の反応式
[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]

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-175ad3f1094f46d29cc66e4971336702
出典データセット
uspto-grants-2006_12
特許番号
US07153960B2

反応ノート

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