Triethylamine → rac-N-[(1R,2S,4S)-bicyclo[2.2.1]hept-2-yl]-5-(morpholin-4-ylcarbonyl)-4-(trifluoromethyl)pyrimidin-2-amine

HRID 38780노트

반응식

HRID 38780 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][O:17][CH2:16][CH2:15]2)=[O:13])=[CH:4][N:3]=1.Cl.[CH:21]12[CH2:27][CH:24]([CH2:25][CH2:26]1)[CH2:23][CH:22]2[NH2:28].C(N(CC)CC)C.O1CCOCC1>O>[C@H:21]12[CH2:27][C@H:24]([CH2:25][CH2:26]1)[CH2:23][C@@H:22]2[NH:28][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][O:17][CH2:16][CH2:15]2)=[O:13])=[CH:4][N:3]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 518934Endo-bicyclo[2.2.1]heptan-2-amine hydrochlorideHCID 581687074-{[2-Chloro-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}morpholine

생성물 1

HCID 66720251rac-N-[(1R,2S,4S)-bicyclo[2.2.1]hept-2-yl]-5-(morpholin-4-ylcarbonyl)-4-(trifluoromethyl)pyrimidin-2-amine수율 70.2%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 4-{[2-chloro-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}morpholine (150 mg), rac-(1S,2R,4R)-bicyclo[2.2.1]heptan-2-amine hydrochloride (300 mg), triethylamine (354 μL), and 1,4-dioxane (1.5 mL) was stirred at room temperature for 3 hours. To the reaction mixture was added water and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate), and the obtained colorless oil was solidified from hexane-ethyl acetate to obtain rac-N-[(1R,2S,4S)-bicyclo[2.2.1]hept-2-yl]-5-(morpholin-4-ylcarbonyl)-4-(trifluoromethyl)pyrimidin-2-amine (132 mg) as a white solid.

후처리

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

출처 및 근거

ORD 기록
ord-8da3856bc8d344a6903de4fb2871ef07
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524727B2

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