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

HRID 2098275Notes

Reaction equation

HRID 2098275 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-2316adc186f7463099a7ace2e4e29165
Source dataset
uspto-grants-2013_05
Patent number
US08450479B2

Reaction notes

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