Water → tert-Butyl 4-[3-(3-thienyl)-1,2,4-thiadiazol-5-yl]piperazine-1-carboxylate

HRID 2263025노트

반응식

HRID 2263025 반응식
Cl[C:2]1[S:6][N:5]=[C:4]([C:7]2[CH:11]=[CH:10][S:9][CH:8]=2)[N:3]=1.[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(N(CC)CC)C.O>CN(C)C=O>[S:9]1[CH:10]=[CH:11][C:7]([C:4]2[N:3]=[C:2]([N:15]3[CH2:14][CH2:13][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]3)[S:6][N:5]=2)=[CH:8]1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 538814275-Chloro-3-(3-thienyl)-1,2,4-thiadiazole

생성물 1

HCID 68778008tert-Butyl 4-[3-(3-thienyl)-1,2,4-thiadiazol-5-yl]piperazine-1-carboxylate수율 86.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 5-chloro-3-(3-thienyl)-1,2,4-thiadiazole (2.47 g, 12.2 mmol) and tert-butyl piperazine-1-carboxylate (2.27 g, 12.2 mmol) in dimethylformamide (25 ml) was added triethylamine (6.8 ml, 48.8 mmol) at room temperature, and the mixture was stirred at room temperature for 1 hour. 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 silica gel column chromatography (hexane: ethyl acetate=9:1) to give 3.72 g (86.5%) of the desired product as a solid.

후처리

  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 silica gel column chromatography (hexane: ethyl acetate=9:1)

출처 및 근거

ORD 기록
ord-a1900776fb0d4ca396e82552dceb5b94
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07851473B2

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