Water → 2-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-8-(2-trifluoromethylphenyl)-5,6-dihydro[1,2,4]triazolo[1,5-a]pyridine

HRID 546794ノート

反応式

HRID 546794 の反応式
[CH3:1][O:2][C:3]1[N:8]=[C:7](/[CH:9]=[CH:10]/[C:11]2[N:30]=[C:14]3[C:15]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([F:29])([F:28])[F:27])(O)[CH2:16][CH2:17][CH2:18][N:13]3[N:12]=2)[CH:6]=[CH:5][C:4]=1[N:31]1[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]1.C(N(S(F)(F)F)CC)C.C(OCC)(=O)C.O>ClCCl>[CH3:1][O:2][C:3]1[N:8]=[C:7](/[CH:9]=[CH:10]/[C:11]2[N:30]=[C:14]3[C:15]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([F:29])([F:28])[F:27])=[CH:16][CH2:17][CH2:18][N:13]3[N:12]=2)[CH:6]=[CH:5][C:4]=1[N:31]1[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]1

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 123472(Diethylamino)sulfur trifluoride2 回HCID 576091932-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-8-(2-trifluoromethylphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-8-ol

生成物 1

HCID 576091762-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-8-(2-trifluoromethylphenyl)-5,6-dihydro[1,2,4]triazolo[1,5-a]pyridine収率 37.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-{(E)-2-[6-Methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-8-(2-trifluoromethylphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-8-ol (56 mg) was dissolved in dichloromethane (2 ml). Diethylaminosulfur trifluoride (45 ul) was added under ice-cooling, and the reaction solution was stirred at room temperature for three hours. Thereafter, diethylaminosulfur trifluoride (45 ul) was added again at room temperature, and the reaction solution was further stirred at room temperature overnight. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration and then the organic layer was concentrated under reduced pressure. The residue was separated by CHIRALPAK™ IB manufactured by Daicel Chemical Industries, Ltd. (2 cm×25 cm; mobile phase: hexane:ethanol=1:1) to obtain the title compound (20 mg). The property values of the compound are as follows.

後処理

  1. temperaturecooling
  2. stirringthe reaction solution was further stirred at room temperature overnight
  3. customthe organic layer was separated
  4. washThe resulting organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe drying agent was separated by filtration
  7. concentrationthe organic layer was concentrated under reduced pressure
  8. customThe residue was separated by CHIRALPAK™ IB

出典と根拠

ORDレコード
ord-e394f6103567411b8ce56411ce54604b
出典データセット
uspto-grants-2011_05
特許番号
US07935815B2

反応ノート

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