Hydrochloric Acid → 3-But-2-ynyl-4-oxo-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid amide
Reaction equation
O[CH2:2][N:3]1[C:8](=[O:9])[N:7]2[CH:10]=[N:11][C:12]([C:13]([NH2:15])=[O:14])=[C:6]2[N:5]=[N:4]1.Br[CH2:17][C:18]#[C:19]C.C1CCN2C(=NCCC2)CC1.Cl>C(#N)C>[CH2:2]([N:3]1[C:8](=[O:9])[N:7]2[CH:10]=[N:11][C:12]([C:13]([NH2:15])=[O:14])=[C:6]2[N:5]=[N:4]1)[C:17]#[C:18][CH3:19]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a cooled solution of 3-(Hydroxymethyl)-4-oxo-3,4-dihydroimidazo[5,1-][1,2,3,5]tetrazine-8-carboxamide (MM-001) (1 equiv) in acetonitrile (0.17 M concentration substrate in solvent) was added the 1-bromo-2-butyne (4 equivs) and DBU (1.4 equivs). The mixture was stirred at this temperature for 30 minutes whereupon it was acidified with 1 N HCl. The mixture was extracted with EtOAc (3×1 reaction volume). The combined organic extracts were combined, dried (MgSO4), filtered and concentrated in vacuo to give an oily residue which was then precipitated from Et2O and washed with further Et2O to give the title compound. 1H NMR (400 MHz, d6-DMSO) δ ppm: 8.84 (1H, s), 7.82 (1H, s), 7.70 (1H, s), 5.08 (2H, q, J=2.4 Hz), 1.84 (3H, t, J=2.4 Hz).
Workup
- extractionThe mixture was extracted with EtOAc (3×1 reaction volume)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto give an oily residue which
- customwas then precipitated from Et2O
- washwashed with further Et2O
Sources & evidence
- ORD record
- ord-355e19cecc9a4d008317651409c70838
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450479B2
Reaction notes
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