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Thiophenol → 7,7-dimethyl-N-(tetrahydro-2H-pyran-2-yloxy)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxamide

HRID 468674
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반응식

HRID 468674 반응식
[CH3:1][C:2]1([CH3:33])[CH2:7][N:6](S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[CH2:5][C:4]2[CH:20]=[C:21]([C:23]([NH:25][O:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][O:28]3)=[O:24])[S:22][C:3]1=2.C(=O)([O-])[O-].[Cs+].[Cs+].C1(S)C=CC=CC=1>C(#N)C>[CH3:1][C:2]1([CH3:33])[CH2:7][NH:6][CH2:5][C:4]2[CH:20]=[C:21]([C:23]([NH:25][O:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][O:28]3)=[O:24])[S:22][C:3]1=2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 7969ThiophenolHCID 10796Cesium carbonateHCID 866513227,7-dimethyl-5-(2-nitrophenylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxamide

생성물 1

HCID 581576817,7-dimethyl-N-(tetrahydro-2H-pyran-2-yloxy)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxamide수율 85.2%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매
2회

실험 절차

To a mixture of 7,7-dimethyl-5-(2-nitrophenylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxamide (15.4 g, 31 mmol) and cesium carbonate (20.2 g, 62 mmol) in acetonitrile (800 mL) was added a solution of thiophenol (6.85 g, 62 mmol) in acetonitrile (70 mL). The reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue applied to silica gel chromatography (0-20% DCM/MeOH) to afford the title compound (8.2 g, 85%). LCMS (FA) ES+ 311; 1H NMR (400 MHz, DMSO) δ 11.49 (s, 1H), 7.30 (s, 1H), 4.91 (s, 1H), 4.01 (dd, J=15.6, 8.0 Hz, 1H), 3.71 (s, 2H), 3.55-3.44 (m, 1H), 2.71 (s, 2H), 1.69 (s, 3H), 1.53 (s, 3H), 1.25 (s, 6H).

후처리

  1. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-c721e43f1fec47b99bafaef00aa4c813
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08624040B2

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