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Hydrochloric Acid → trans-2-(4,6-Dimethoxypyrimidin-2-yl)oxy-N-benzenesulphonylcyclohexanecarboxamide

HRID 21896
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HRID 21896 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[C:18]([OH:20])=O)[N:4]=1.[C:21]1([S:27]([NH2:30])(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.N12CCCN=C1CCCCC2.Cl>O1CCCC1>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([O:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[C:18]([NH:30][S:27]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:29])=[O:28])=[O:20])[N:6]=1
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참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 7370BenzenesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15728507trans-2-(4,6-Dimethoxypyrimidin-2-yl)oxycyclohexanecarboxylic acid

생성물 1

HCID 15239633trans-2-(4,6-Dimethoxypyrimidin-2-yl)oxy-N-benzenesulphonylcyclohexanecarboxamide수율 6.7%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
3회

실험 절차

trans-2-(4,6-Dimethoxypyrimidin-2-yl)oxycyclohexanecarboxylic acid (1.0 g), prepared as in Example 11, in dry tetrahydrofuran (10 ml) was added dropwise to a stirred solution of 1,1-carbonyldiimidazole (0.57 g) in dry tetrahydrofuran (10 ml) under nitrogen. The reaction mixture was stirred 30 minutes at ambient temperature, heated to reflux for 30 minutes and cooled to ambient temperature. Benzenesulphonamide (0.56 g) was added followed by dropwise addition of 1,8-diazabicyclo (5.4.0) undec-7-ene (0.54) in dry tetrahydrofuran (5 ml). The reaction mixture was stirred for 24 hours at ambient temperature, refluxed for 6 hours then poured into 1N hydrochloric acid (80 ml) and extracted with 3×100 ml portions of diethyl ether. The combined ether extracts were dried over magnesium sulphate and evaporated. The residue was chromatographed on silica-gel, using a 2:1 dichloromethane/ethyl acetate eluant, to give 100 mg of the title compound, melting point 175° C.

후처리

  1. temperatureheated
  2. temperatureto reflux for 30 minutes
  3. temperaturecooled to ambient temperature
  4. stirringThe reaction mixture was stirred for 24 hours at ambient temperature
  5. temperaturerefluxed for 6 hours
  6. extractionextracted with 3×100 ml portions of diethyl ether
  7. dry with materialThe combined ether extracts were dried over magnesium sulphate
  8. customevaporated
  9. customThe residue was chromatographed on silica-gel

출처 및 근거

ORD 기록
ord-66998b7f00e74f96b7a19de6d7beba6e
출처 데이터셋
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05426090

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