Ethylene Glycol → tert-Butyl 4-[4-(2-hydroxyethoxy)-1,2,5-thiadiazol-3-yl]-1-piperazinecarboxylate

HRID 493354

반응식

HRID 493354 반응식
Cl[C:2]1[C:3]([N:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)=[N:4][S:5][N:6]=1.[CH2:20]([OH:23])[CH2:21][OH:22]>N1C=CC=CC=1.CCOC(C)=O>[OH:22][CH2:21][CH2:20][O:23][C:2]1[C:3]([N:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)=[N:4][S:5][N:6]=1

참가 물질

5

반응물 2

HCID 174Ethylene GlycolHCID 15524001Tert-butyl 4-(4-chloro-1,2,5-thiadiazol-3-yl)piperazine-1-carboxylate

생성물 1

HCID 22036393tert-Butyl 4-[4-(2-hydroxyethoxy)-1,2,5-thiadiazol-3-yl]-1-piperazinecarboxylate수율 79.6%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

K-t-BuO (1.24 g, 11 mmol) was added to a mixture of the product obtained in Step 1 (1.98 g, 6.5 mmol) and ethylene glycol (2.54 ml, 45.5 mmol) in pyridine (15 ml). The reaction mixture was stirred at 100° C. for 6 h and at room temperature overnight. The solution was then poured into ice-water and diluted with EtOAc. The organic phase was dried (MgSO4) and the solvent removed under reduced pressure. The residue was purified by chromatography on silica gel eluting hexane/EtOAc (1:1) to give 1.71 g (65%) of title product as an orange oil. MS m/z 331 (M+H)+. Step 3: tert-Butyl 4-(4-{2-[(2-oxo-2H-chromen-7-yl)oxy]ethoxy}-1,2,5-thiadiazol-3-yl)-1-piperazinecarboxylate.

후처리

  1. dry with materialThe organic phase was dried (MgSO4)
  2. customthe solvent removed under reduced pressure
  3. customThe residue was purified by chromatography on silica gel
  4. washeluting hexane/EtOAc (1:1)

출처 및 근거

ORD 기록
ord-d8773e0f72734dd2b36822a2fdc898cf
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07534794B2

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