1,3-Cyclohexanediol → (3-hydroxycyclohexyl) 2-(4-fluoroanilino)-4-oxo-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylidene)furan-3-carboxylate

HRID 402703

反応式

HRID 402703 の反応式
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]2[O:15][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[C:13]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:12]2=[O:29])=[CH:2]1.[CH:30]1(O)[CH2:35]CC[CH:32]([OH:36])[CH2:31]1>CN(C)C(=O)C.[Zn]>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]2[O:15][C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)=[C:13]([C:24]([O:26][CH:27]3[CH2:35][CH2:30][CH2:31][CH:32]([OH:36])[CH2:28]3)=[O:25])[C:12]2=[O:29])=[CH:2]1

参加物

5

反応物 2

HCID 104331,3-CyclohexanediolHCID 178469558ethyl 2-(4-fluoroanilino)-4-oxo-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylidene)furan-3-carboxylate

生成物 1

HCID 178524383(3-hydroxycyclohexyl) 2-(4-fluoroanilino)-4-oxo-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylidene)furan-3-carboxylate収率 13%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 31374Dimethylacetamide溶媒

実験手順

A solution of the compound (0.10 g, 0.25 mmol) of Example 21, 1,3-cyclohexanediol (0.44 g, 3.8 mmol) and zinc cluster catalyst (Zn4(OCOCF3)6O) (0.018 g, 0.019 mmol) in N,N-dimethylacetamide (1.0 mL) was stirred at 130° C. for 1.5 days. Cooled to ambient temperature, the precipitate was removed by filtration. The filtrate was purified by preparative HPLC to afford the titled compound as solid (0.010 g, y. 13%).

後処理

  1. customthe precipitate was removed by filtration
  2. customThe filtrate was purified by preparative HPLC

出典と根拠

ORDレコード
ord-aa96d85647734d7882ecbe0903cc6797
出典データセット
uspto-grants-2014_06
特許番号
US08742113B2

関連ノート

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