Dimethylamine → HCID 57743004, 화합물

HRID 2043609노트

반응식

HRID 2043609 반응식
Cl[C:2]1[S:3][C:4]([CH2:7][N:8]2[CH2:12][CH:11]([C:13]3[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[C:14]=3[F:21])[CH2:10][C:9]2=[O:22])=[CH:5][N:6]=1.[CH3:23][NH:24][CH3:25].O[Li].O>C1COCC1.O>[CH3:23][N:24]([CH3:25])[C:2]1[S:3][C:4]([CH2:7][N:8]2[CH2:12][CH:11]([C:13]3[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[C:14]=3[F:21])[CH2:10][C:9]2=[O:22])=[CH:5][N:6]=1

참가 물질

6

반응물 3

HCID 674Dimethylamine2회HCID 168937Lithium hydroxide, monohydrateHCID 57742995HCID 57742995, 화합물

생성물 1

HCID 57743004HCID 57743004, 화합물수율 32.3%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

In a sealed tube fitted with a magnetic stirrer, 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-4-(2,3,5-trifluorophenyl)pyrrolidin-2-one 250 (0.3 g, 0.87 mmol) is dissolved in a mixture of THF (4 ml) and H2O (0.1 ml). Dimethylamine (0.85 ml, 1.7 mmol) and LiOH.H2O (0.043 g, 1 mmol) are added and the mixture is stirred at room temperature for 12 h and heated at 50° C. overnight. Dimethylamine (3×3.4 mmol, then 1×5.1 mmol) is added after 24 h, 48 h, 72 h and 96 h heating. THF is evaporated, the residue is dissolved in water and CH2Cl2, the pH of the aqueous phase is brought to 9 and the aqueous phase is extrated with CH2Cl2. The combined organic phases are dried over MgSO4, filtered and concentrated. The crude product is purified by chromatography on silicagel and recrystallized from diisopropylether to afford 0.1 g of 1-{[2-(dimethylamino)-1,3-thiazol-5-yl]methyl}-4-(2,3,5-trifluorophenyl)pyrrolidin-2-one 251.

후처리

  1. customIn a sealed tube fitted with a magnetic stirrer
  2. temperatureheated at 50° C. overnight
  3. temperatureheating
  4. customTHF is evaporated
  5. dissolutionthe residue is dissolved in water
  6. dry with materialThe combined organic phases are dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product is purified by chromatography on silicagel
  10. customrecrystallized from diisopropylether

출처 및 근거

ORD 기록
ord-af2aac9f76d34d72b4cd8c009292be2b
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586623B2

반응 노트

불러오는 중…