Ethyl 2-(8-carbamoyl-4-oxoimidazo[5,1-d][1,2,3,5]tetrazin-3(4H)-yl)acetate → 2-(8-Carbamoyl-4-oxoimidazo[5,1-d][1,2,3,5]tetrazin-3(4H)-yl)acetic acid

HRID 2098278Notes

Reaction equation

[C:1]([C:4]1[N:5]=[CH:6][N:7]2[C:12](=[O:13])[N:11]([CH2:14][C:15]([O:17]CC)=[O:16])[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][C:15]([OH:17])=[O:16])[N:10]=[N:9][C:8]=12)(=[O:3])[NH2:2]

Participants

Conditions

Temperature: 42.5 °C

Procedure

Ethyl 8-Carbamoyl-3,4-dihydro-4-oxoimidazo[5,1-d]-1,2,3,5-tetrazin-3-ylacetate (10.2 g) was suspended in hydrochloric acid (5 M, 50 mL). The suspension was stirred for 4 hours at 40-45° C. until hydrolysis was complete (TLC). The mixture was concentrated under reduced pressure to 20 mL and the solid product was collected and washed with acetone (3×20 mL). The product was dried under high vacuum to give the title compound. LCMS (ES−), m/z 237 (M−H−) in the solvent front. Yield 25.04%.

Workup

concentrationThe mixture was concentrated under reduced pressure to 20 mL
customthe solid product was collected
washwashed with acetone (3×20 mL)
customThe product was dried under high vacuum

Sources & evidence

ORD record: ord-97f4e13c05d94124ac1e1e47018f216f
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450479B2

Reaction notes

Loading…