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Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → 6'-(5-methyl-1H-pyrazol-4-yl)-4-phenyl-1'H-spiro [cyclohexane-1,2'-thieno[3,2-d]pyrimidin]-4'(3'H)-one

HRID 2364092
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인쇄 미리보기

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HRID 2364092 반응식
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[N:9][NH:10][C:11]=2[CH3:12])[S:4][C:3]=1[C:13]([NH2:15])=[O:14].[C:16]1([CH:22]2[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[O-]S([O-])(=O)=O.[Mg+2].CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.C([O-])(O)=O.[Na+]>CCOC(C)=O.C1COCC1.CC(N(C)C)=O>[CH3:12][C:11]1[NH:10][N:9]=[CH:8][C:7]=1[C:5]1[S:4][C:3]2[C:13](=[O:14])[NH:15][C:25]3([CH2:24][CH2:23][CH:22]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:27][CH2:26]3)[NH:1][C:2]=2[CH:6]=1
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참가 물질

8

반응물 5

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 24083Sulfuric acid magnesium salt (1:1)HCID 786054-PhenylcyclohexanoneHCID 516892Sodium BicarbonateHCID 667430133-amino-5-(5-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamide

생성물 1

HCID 66743245
6'-(5-methyl-1H-pyrazol-4-yl)-4-phenyl-1'H-spiro [cyclohexane-1,2'-thieno[3,2-d]pyrimidin]-4'(3'H)-one

시약·촉매·용매 2

HCID 31374Dimethylacetamide용매HCID 21939870Tetrahydrofuran ethyl acetate용매

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온도
80 °C

실험 절차

A mixture of 3-amino-5-(5-methyl-1H-pyrazol-4-yl) thiophene-2-carboxamide (111 mg, 0.50 mmol), 4-phenylcyclohexanone (261 mg, 1.50 mmol), MgSO4 (120 mg, 1.00 mmol), CSA (11.61 mg, 0.050 mmol) and DMA (3 mL) was stirred at 80° C. for 1 h. The mixture was poured into saturated aqueous NaHCO3 and 2:1 EtOAc/THF. The precipitate was collected by filtration and washed with water and EtOAc to give the title compound (28.7 mg, 15%, single isomer on cyclohexane, absolute structure not determined) as gray solid:

후처리

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water and EtOAc

출처 및 근거

ORD 기록
ord-83c0bb06fb1f46898238a21be4083d77
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08691828B2

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