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Cyclopentanone → 1'-ethyl-6'-(pyridin-4-yl)-1'H-spiro [cyclopentane-1,2'-thieno[3,2-d]pyrimidin]-4'(3'H)-one

HRID 2363962
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HRID 2363962 반응식
[CH2:1]([NH:3][C:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[S:6][C:5]=1[C:15]([NH2:17])=[O:16])[CH3:2].[C:18]1(=O)[CH2:22][CH2:21][CH2:20][CH2:19]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH2:1]([N:3]1[C:4]2[CH:8]=[C:7]([C:9]3[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=3)[S:6][C:5]=2[C:15](=[O:16])[NH:17][C:18]21[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH3:2]
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참가 물질

6

반응물 4

HCID 8452CyclopentanoneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 667438263-(Ethylamino)-5-(pyridin-4-yl)thiophene-2-carboxamide

생성물 1

HCID 468982461'-ethyl-6'-(pyridin-4-yl)-1'H-spiro [cyclopentane-1,2'-thieno[3,2-d]pyrimidin]-4'(3'H)-one수율 28%

시약·촉매·용매 1

HCID 176
Acetic Acid
용매

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온도
100 °C

실험 절차

A mixture of 3-(ethylamino)-5-(pyridin-4-yl)thiophene-2-carboxamide (0.100 g, 0.400 mmol), cyclopentanone (2.0 mL), p-toluenesulfonic acid monohydrate (0.0095 g, 0.050 mmol) and acetic acid (2.0 mL) was stirred for 2 h at 100° C. in a sealed tube. The mixture was poured into sat. aqueous sodium hydrogen carbonate (150 mL). Extraction with ethyl acetate (100 mL, 50 mL), drying over magnesium sulfate, filtration and concentration at reduced pressure gave an oil. This oil was purified by column chromatography (Combiflash, 40 g silica gel, dichloromethane to ethyl acetate), then triturated with ethyl acetate, and the precipitate was collected by filtration to afford the title compound (0.0434 g, 28%) as a yellow solid:

후처리

  1. extractionExtraction with ethyl acetate (100 mL, 50 mL)
  2. dry with materialdrying over magnesium sulfate, filtration and concentration at reduced pressure
  3. customgave an oil
  4. customThis oil was purified by column chromatography (Combiflash, 40 g silica gel, dichloromethane to ethyl acetate)
  5. customtriturated with ethyl acetate
  6. filtrationthe precipitate was collected by filtration

출처 및 근거

ORD 기록
ord-f48b2b30247e4b719b377904ce302135
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08691828B2

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