1,4-Dioxane → rac-[(1R,2S,3R,4S)-3-({5-[(1,1-dioxidothiomorpholin-4-yl)carbonyl]-4-(trifluoromethyl)pyrimidin-2-yl}amino)bicyclo[2.2.1]hept-2-yl]methanol

HRID 38781노트

반응식

HRID 38781 반응식
Cl[C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12]([N:14]2[CH2:19][CH2:18][S:17](=[O:21])(=[O:20])[CH2:16][CH2:15]2)=[O:13])=[CH:4][N:3]=1.[O:22]1[CH2:27][CH2:26]OCC1.C([N:31]([CH2:35][CH3:36])C(C)C)(C)C>O>[O:20]=[S:17]1(=[O:21])[CH2:18][CH2:19][N:14]([C:12]([C:5]2[C:6]([C:8]([F:11])([F:10])[F:9])=[N:7][C:2]([NH:31][C@@H:35]3[C@@H:36]4[CH2:4][C@@H:5]([CH2:6][CH2:8]4)[C@@H:26]3[CH2:27][OH:22])=[N:3][CH:4]=2)=[O:13])[CH2:15][CH2:16]1

참가 물질

5

반응물 3

HCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 581689914-{[2-Chloro-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}thiomorpholine 1,1-dioxide

생성물 1

HCID 66720222rac-[(1R,2S,3R,4S)-3-({5-[(1,1-dioxidothiomorpholin-4-yl)carbonyl]-4-(trifluoromethyl)pyrimidin-2-yl}amino)bicyclo[2.2.1]hept-2-yl]methanol

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

To a mixture of 4-{[2-chloro-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}thiomorpholin-1,1-dioxide (100 mg), 3-exo-hydroxymethylbicyclo[2.2.1]heptyl-2-exo-amine hydrochloride (129 mg), and 1,4-dioxane (3 mL) was added N,N-diisopropyl ethylamine (0.20 mL) at room temperature, and the mixture was stirred at 80° C. for 2 hours. To the reaction mixture was added water and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to obtain rac-[(1R,2S,3R,4S)-3-({5-[(1,1-dioxidothiomorpholin-4-yl)carbonyl]-4-(trifluoromethyl)pyrimidin-2-yl}amino)bicyclo[2.2.1]hept-2-yl]methanol (72 mg) as a white solid.

후처리

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-eaee6ecfb9a640bcb15d47a5c9aa967b
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524727B2

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