Hydrochloric Acid → 3-(8-Carbamoyl-oxoimidazo[5,1-d][1,2,3,5]tetrazin-3(4H)-yl)propanoic acid

HRID 2098276Notes

Reaction equation

HRID 2098276 reaction equation
[C:1]([C:4]1[N:5]=[CH:6][N:7]2[C:12](=[O:13])[N:11]([CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])[N:10]=[N:9][C:8]=12)(=[O:3])[NH2:2].Cl>>[C:1]([C:4]1[N:5]=[CH:6][N:7]2[C:12](=[O:13])[N:11]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])[N:10]=[N:9][C:8]=12)(=[O:3])[NH2:2]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 44128731Ethyl 3-(8-carbamoyl-oxoimidazo[5,1-d][1,2,3,5]tetrazin-3(4H)-yl)propanoate

Product 1

HCID 441286543-(8-Carbamoyl-oxoimidazo[5,1-d][1,2,3,5]tetrazin-3(4H)-yl)propanoic acid

Conditions

Temperature
45 °C

Procedure

A suspension of ethyl 3-(8-carbamoyl-oxoimidazo[5,1-d][1,2,3,5]tetrazin-3(4H)-yl)propanoate (0.5 g, 1.784 mmol) in 5 M hydrochloric acid (2.34 mL, 11.70 mmol) was heated at 45° C. After 16 hours, the reaction mixture was filtered and the residue was washed with water (5 mL) and acetone (5 mL). A portion (50 mg from a total of 332 mg) was recrystallized from hot acetonitrile/water to afford the title compound as an off white solid. Yield: 32 mg, 0.13 mmol, 47% pro rata. LCMS (ES+), m/z 281 (M+H)+ at the solvent front. 1H NMR (400 MHz, d6-DMSO) δ: 12.5 (1H, br s), 8.80 (1H, s), 7.75 (1H, br s), 7.65 (1H, br s), 4.45 (2H, t), 2.75 (2H, t).

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthe residue was washed with water (5 mL) and acetone (5 mL)
  3. customA portion (50 mg from a total of 332 mg) was recrystallized from hot acetonitrile/water

Sources & evidence

ORD record
ord-19dc8bb9e3b2426ba8cbdc1bac8f7c2f
Source dataset
uspto-grants-2013_05
Patent number
US08450479B2

Reaction notes

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