Dimethylamine → HCID 57743004、化合物

HRID 1926760ノート

反応式

HRID 1926760 の反応式
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

参加物

6

反応物 3

HCID 674Dimethylamine2 回HCID 168937Lithium hydroxide, monohydrateHCID 57742995HCID 57742995、化合物

生成物 1

HCID 57743004HCID 57743004、化合物収率 32.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7add6557a3214cfb98eb6ad29cb27532
出典データセット
uspto-grants-2012_05
特許番号
US08183241B2

反応ノート

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