Ethyl 3-isocyanatopropanoate → Ethyl 3-(8-carbamoyl-oxoimidazo[5,1-d][1,2,3,5]tetrazin-3(4H)-yl)propanoate

HRID 2098275ノート

反応式

HRID 2098275 の反応式
[N:1]([CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:2]=[O:3].[N+:11](=[C:13]1[N:17]=[CH:16][N:15]=[C:14]1[C:18]([NH2:20])=[O:19])=[N-:12]>CS(C)=O>[C:18]([C:14]1[N:15]=[CH:16][N:17]2[C:2](=[O:3])[N:1]([CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:12]=[N:11][C:13]=12)(=[O:19])[NH2:20]

参加物

4

反応物 2

HCID 2733373Ethyl 3-isocyanatopropanoateHCID 534265854-Diazo-4H-imidazole-5-carboxamide

生成物 1

HCID 44128731Ethyl 3-(8-carbamoyl-oxoimidazo[5,1-d][1,2,3,5]tetrazin-3(4H)-yl)propanoate

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Ethyl 3-isocyanatopropionate (Alfa Lancaster) (0.504 mL, 3.83 mmol) was added drop wise to a suspension of 5-diazoimidazole-4-carboxamide (0.450 g, 3.65 mmol) in dry dimethylsulfoxide (4.5 mL) at room temperature under nitrogen. The reaction was stirred in the dark at room temperature. After 16 hours, the reaction mixture was poured onto ice (approximately 25 mL) and the resulting precipitate was washed with ethyl acetate (10 mL) and ether (10 mL) to afford the title compound as a pale brown solid. Yield: 770 mg, 2.75 mmol, 75%. LCMS (ES+), m/z 281 (M+H)+ at 1.60 minutes. 1H NMR (400 MHz, d6-DMSO) δ: 8.86 (1H, s), 7.75 (1H, br s), 7.62 (1H, br s), 4.51 (2H, t), 4.07 (2H, q), 2.89 (2H, t), 1.17 (3H, t).

後処理

  1. additionthe reaction mixture was poured onto ice (approximately 25 mL)
  2. washthe resulting precipitate was washed with ethyl acetate (10 mL) and ether (10 mL)

出典と根拠

ORDレコード
ord-2316adc186f7463099a7ace2e4e29165
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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