Dimethylamine → HCID 57743004, 화합물

HRID 1926760노트

반응식

HRID 1926760 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 extracted 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. extractionthe aqueous phase is extracted with CH2Cl2
  7. dry with materialThe combined organic phases are dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product is purified by chromatography on silicagel
  11. customrecrystallized from diisopropylether

출처 및 근거

ORD 기록
ord-7add6557a3214cfb98eb6ad29cb27532
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183241B2

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