Hydrochloric Acid → methyl rac-2-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-ylamino]-4-(trifluoromethyl)pyrimidine-5-carboxylate

HRID 38763

반응식

HRID 38763 반응식
Cl[C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][N:3]=1.[CH:16]12[CH2:22][CH:19]([CH2:20][CH2:21]1)[CH2:18][CH:17]2[NH2:23].C(N(CC)C(C)C)(C)C.Cl>O.O1CCOCC1>[C@H:16]12[CH2:22][C@H:19]([CH2:20][CH2:21]1)[CH2:18][C@H:17]2[NH:23][C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][N:3]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 98480Exo-2-bornanamineHCID 3696469Methyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate

생성물 1

HCID 66720228methyl rac-2-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-ylamino]-4-(trifluoromethyl)pyrimidine-5-carboxylate수율 99.2%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

To a mixture of methyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate (4.0 g), rac-(1R,2R,4S)-bicyclo[2.2.1]heptan-2-amine (3.7 g), and 1,4-dioxane (60 mL) was added N,N-diisopropyl ethylamine (4.3 mL) at room temperature, and the mixture was stirred at the same temperature for 19 hours. To the reaction mixture were added water and 1 M hydrochloric acid, followed by extraction 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 to obtain methyl rac-2-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-ylamino]-4-(trifluoromethyl)pyrimidine-5-carboxylate (5.2 g) as a yellowish white solid.

후처리

  1. extractionfollowed by extraction 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

출처 및 근거

ORD 기록
ord-b31c89843f824f2591d57d6670ce90d7
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524727B2

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