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

HRID 2098275노트

반응식

HRID 2098275 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2316adc186f7463099a7ace2e4e29165
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450479B2

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