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 2098284ノート

反応式

HRID 2098284 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-60ee976f646b447eabde9485ee76fe53
出典データセット
uspto-grants-2013_05
特許番号
US08450479B2

反応ノート

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