Water → HCID 68777272、化合物

HRID 2262964ノート

反応式

HRID 2262964 の反応式
[N:1]1([C:7]2[O:11][C:10]([NH:12][C:13](=[O:20])OCC(Cl)(Cl)Cl)=[N:9][N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:21]1([C:27]2[N:31]=[C:30]([N:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[S:29][N:28]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[N:1]1([C:7]2[O:11][C:10]([NH:12][C:13]([N:35]3[CH2:36][CH2:37][N:32]([C:30]4[S:29][N:28]=[C:27]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[N:31]=4)[CH2:33][CH2:34]3)=[O:20])=[N:9][N:8]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

参加物

6

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazineHCID 86625481HCID 86625481、化合物

生成物 1

HCID 68777272HCID 68777272、化合物収率 9%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

A mixed solution of 2,2,2-trichloroethyl (5-morpholin-4-yl-1,3,4-oxadiazol-2-yl)carbamate (269 mg, 0.777 mmol), 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (211 mg, 0.854 mmol) and diisopropylethylamine (0.149 ml, 0.854 mmol) in dimethyl sulfoxide (2.5 ml) was stirred at 70° C. for 3 hours. Water was poured to the reaction mixture, and the resulting solution was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by high performance liquid chromatography (YMC HPLC Column eluted with 10% to 100% Liquid A; Liquid A: a 0.1% solution of trifluoroacetic acid in acetonitrile; Liquid B: an aqueous 0.1% trifluoroacetic acid solution) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 31 mg (9.0%) of the desired product as a solid.

後処理

  1. extractionthe resulting solution was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by high performance liquid chromatography (YMC HPLC Column
  6. washeluted with 10% to 100% Liquid A
  7. customLiquid B: an aqueous 0.1% trifluoroacetic acid solution) and recrystallized from a mixed solvent of hexane and tetrahydrofuran

出典と根拠

ORDレコード
ord-231493dcfd3d49a0ae60a690e657a2bf
出典データセット
uspto-grants-2010_12
特許番号
US07851473B2

反応ノート

読み込み中…