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Sodium methanethiolate → 3-[(1S,2S)-2-Hydroxycyclohexyl]-6-{[6-(methylthio)pyridine-3-yl]methyl}pyrido[3,4-h]quinazolin-4(3H)-one

HRID 1183823
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HRID 1183823 반응식
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:10]=[C:11]3[C:16](=[C:17]4[CH:22]=[CH:21][N:20]=[CH:19][C:18]=24)[N:15]=[CH:14][N:13]([C@H:23]2[CH2:28][CH2:27][CH2:26][CH2:25][C@@H:24]2[OH:29])[C:12]3=[O:30])=[CH:4][CH:3]=1.[CH3:31][S-:32].[Na+]>CN(C=O)C.C(OCC)(=O)C>[OH:29][C@H:24]1[CH2:25][CH2:26][CH2:27][CH2:28][C@@H:23]1[N:13]1[C:12](=[O:30])[C:11]2[C:16](=[C:17]3[CH:22]=[CH:21][N:20]=[CH:19][C:18]3=[C:9]([CH2:8][C:5]3[CH:6]=[N:7][C:2]([S:32][CH3:31])=[CH:3][CH:4]=3)[CH:10]=2)[N:15]=[CH:14]1
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5

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HCID 4378561Sodium methanethiolateHCID 532612286-[(6-Chloropyridin-3-yl)methyl]-3-[(1S,2S)-2-hydroxycyclohexyl]pyrido[3,4-h]quinazolin-4(3H)-one

생성물 1

HCID 532612323-[(1S,2S)-2-Hydroxycyclohexyl]-6-{[6-(methylthio)pyridine-3-yl]methyl}pyrido[3,4-h]quinazolin-4(3H)-one

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate
용매

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온도
130 °C

실험 절차

To a solution of 6-[(6-chloropyridin-3-yl)methyl]-3-[(1S,2S)-2-hydroxycyclohexyl]pyrido[3,4-h]quinazolin-4(3H)-one (Example 1, 0.120 g, 0.285 mmol) in 2 mL of DMF was added sodium thiomethoxide (0.100 g, 1.43 mmol). The mixture was heated in a sealed tube at 130° C. for 18 h, cooled to rt, and diluted with ethyl acetate. The organic solution was washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-5% methanol in dichloromethane, to provide the title compound that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 432.9 for [M+H]+: 1H NMR (400 MHz, CDCl3) δ 9.41 (s, 1H), 8.73-8.63 (m, 2H), 8.39 (s, 1H), 8.29-8.19 (m, 1H), 8.09 (s, 1H), 7.32-7.26 (m, 1H), 7.08 (d, J=8.3 Hz, 1H), 4.61 (br s, 1H), 4.50 (s, 2H), 4.05 (br s, 1H), 2.53 (s, 3H), 2.40-2.27 (m, 2H), 2.13-1.75 (m, 3H), 1.55-1.35 (m, 3H).

후처리

  1. temperaturecooled to rt
  2. washThe organic solution was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified via silica gel chromatography
  7. washeluting with 0-5% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-27f059cd6e784458a021b0b9c5e664bf
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08664387B2

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