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Trifluoroacetic acid → 1-(4-Chloro-phenyl)-6-(4-iodo-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c)pyridine-3-carboxylic acid methyl ester

HRID 860831
ノート
印刷プレビュー

反応式

HRID 860831 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:13]2[C:8](N3CCOCC3)([C:9](=[O:21])[N:10]([C:14]3[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=3)[CH2:11][CH2:12]2)[N:7]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)[N:6]=1)=[O:4].FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:13]2[CH2:12][CH2:11][N:10]([C:14]3[CH:15]=[CH:16][C:17]([I:20])=[CH:18][CH:19]=3)[C:9](=[O:21])[C:8]=2[N:7]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)[N:6]=1)=[O:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 694457171-(4-Chloro-phenyl)-6-(4-iodo-phenyl)-7a-morpholin-4-yl-7-oxo-3a,4,5,6,7,7a-hexahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid methyl ester

生成物 1

HCID 587660011-(4-Chloro-phenyl)-6-(4-iodo-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c)pyridine-3-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

A solution of 1-(4-chloro-phenyl)-6-(4-iodo-phenyl)-7a-morpholin-4-yl-7-oxo-3a,4,5,6,7,7a-hexahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid methyl ester (52, 595 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, 5–20% EtOAc/hexane gradient elution) to afford the desired elimination product (53, 467 mg, 508 mg theoretical, 92%) as a pale-yellow oil, which solidified upon standing at room temperature in vacuo. For 53, CIMS m/z 508/510 (M++H, C20H15ClIN3O3).

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, 5–20% EtOAc/hexane gradient elution)
  4. customto afford the desired elimination product (53, 467 mg, 508 mg theoretical, 92%) 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-054e8fdb5c1846eb817b087f0d28d972
出典データセット
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07153960B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート