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

HRID 2363930노트

반응식

HRID 2363930 반응식
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[S:4][C:3]=1[C:13]([NH2:15])=[O:14].[C:16]1(=O)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[N:10]1[CH:9]=[CH:8][C:7]([C:5]2[S:4][C:3]3[C:13](=[O:14])[NH:15][C:16]4([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]4)[NH:1][C:2]=3[CH:6]=2)=[CH:12][CH:11]=1

참가 물질

6

반응물 4

HCID 7967CyclohexanoneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 99208523-Amino-5-(pyridin-4-yl)thiophene-2-carboxamide

생성물 1

HCID 667442146'-(pyridin-4-yl)-1'H-spiro[cyclohexane-1,2'-thieno[3,2-d]pyrimidin]-4'(3'H)-one수율 36%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
90 °C

실험 절차

A mixture of 3-amino-5-(pyridin-4-yl)thiophene-2-carboxamide (0.110 g, 0.500 mmol), cyclohexanone (0.245 g, 2.50 mmol), p-toluenesulfonic acid monohydrate (0.105 g, 0.550 mmol) and toluene (5.0 mL) was stirred for 1 h at 90° C. The mixture was poured into aqueous sodium hydrogen carbonate (30 mL). Extraction with ethyl acetate/tetrahydrofuran (2:1, 2×30 mL), drying over magnesium sulfate, filtration and concentration at reduced pressure gave an oil. The oil was purified by column chromatography (12 g, silica, Combiflash, dichloromethane to 80:20 dichloromethane/methanol) to afford the title compound (0.053 g, 36%) as a yellow solid:

후처리

  1. extractionExtraction with ethyl acetate/tetrahydrofuran (2:1, 2×30 mL)
  2. dry with materialdrying over magnesium sulfate, filtration and concentration at reduced pressure
  3. customgave an oil
  4. customThe oil was purified by column chromatography (12 g, silica, Combiflash, dichloromethane to 80:20 dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-bd603f2baa414cc783da7f502decb352
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691828B2

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