4-Diazo-4H-imidazole-5-carboxamide → 3-(2-(tert-Butyldimethylsilyloxy)ethyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

HRID 2098284노트

반응식

HRID 2098284 반응식
[Si:1]([O:8][CH2:9][CH2:10][N:11]=[C:12]=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N+:14](=[C:16]1[N:20]=[CH:19][N:18]=[C:17]1[C:21]([NH2:23])=[O:22])=[N-:15]>CS(C)=O>[Si:1]([O:8][CH2:9][CH2:10][N:11]1[C:12](=[O:13])[N:20]2[CH:19]=[N:18][C:17]([C:21]([NH2:23])=[O:22])=[C:16]2[N:14]=[N:15]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 534265854-Diazo-4H-imidazole-5-carboxamideHCID 595674552-(Tert-butyldimethylsilyloxy)ethyl isocyanate

생성물 1

HCID 441288053-(2-(tert-Butyldimethylsilyloxy)ethyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

Crude 2-(tert-butyldimethylsilyloxy)ethyl isocyanate (422 mg, 2.097 mmol) was added drop wise to a solution of 5-diazoimidazole-4-carboxamide (250 mg, 1.823 mmol) in dimethylsulfoxide (2.5 mL) and the reaction mixture was stirred at room temperature. After 16 hours, the crude reaction mixture was applied to reverse phase silica (C18 silica) and eluted with water and then acetonitrile. The acetonitrile fractions were combined and purified by flash column chromatography (SiO2, gradient 0-100% acetonitrile in dichloromethane) to furnish the title compound as a white solid. Yield: 40 mg, 0.12 mmol, 6.5%. LCMS (ES+) m/z 339 (M+H)+ at 3.19 minutes. 1H NMR (400 MHz, d6-DMSO) δ: 8.87 (1H, s), 7.83 (1H, br s), 7.70 (1H, bs), 4.41 (2H, t), 3.98 (2H, t), 0.78 (9H, t), −0.03 (6H, s).

후처리

  1. customthe crude reaction mixture
  2. washeluted with water
  3. custompurified by flash column chromatography (SiO2, gradient 0-100% acetonitrile in dichloromethane)

출처 및 근거

ORD 기록
ord-60ee976f646b447eabde9485ee76fe53
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450479B2

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