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

HRID 402703

반응식

HRID 402703 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 31374Dimethylacetamide용매

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-aa96d85647734d7882ecbe0903cc6797
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742113B2

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