Acetic Acid → 3-(2-Hydroxyethyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

HRID 2098285Notes

Reaction equation

HRID 2098285 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[C:16](=[O:17])[N:15]2[CH:18]=[N:19][C:20]([C:21]([NH2:23])=[O:22])=[C:14]2[N:13]=[N:12]1)(C(C)(C)C)(C)C.CC(O)=O.O>C1COCC1>[OH:8][CH2:9][CH2:10][N:11]1[C:16](=[O:17])[N:15]2[CH:18]=[N:19][C:20]([C:21]([NH2:23])=[O:22])=[C:14]2[N:13]=[N:12]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 441288053-(2-(tert-Butyldimethylsilyloxy)ethyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

Product 1

HCID 441288063-(2-Hydroxyethyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(2-(tert-butyldimethylsilyloxy)ethyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide (50 mg, 0.148 mmol) in THF:AcOH:water (5 mL of a 1:3:1 v/v/v mixture) was stirred at room temperature. After 3 hours, the reaction mixture was concentrated in vacuo and the residue was purified by flash column chromatography (SiO2, gradient 0-100% acetonitrile in dichloromethane) to furnish the title compound as a white solid. Yield: 15 mg, 0.067 mmol, 45%. LCMS (ES+) m/z 225 (M+H)+ at 0.62 minutes. 1H NMR (400 MHz, d6-DMSO) δ: 8.84 (1H, s), 7.81 (1H, br s), 7.68 (1H, bs), 4.85 (1H, t) 4.34 (2H, t), 3.79 (2H, q).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by flash column chromatography (SiO2, gradient 0-100% acetonitrile in dichloromethane)

Sources & evidence

ORD record
ord-c94c1114491a4d43a3169190dd4bdfe1
Source dataset
uspto-grants-2013_05
Patent number
US08450479B2

Reaction notes

Loading…