Triethylamine → 7-[2,3-bis(tert-butoxycarbonyl)guanidino]-2,3-dihydro-1H-imidazo[1,2-b]pyrazole
Reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:11]=[N:10][N:9]2[CH2:12][CH2:13][NH:14][C:8]=12.C(N(CC)CC)C.[C:22]([O:26][C:27]([NH:29][C:30]([NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=NS(C(F)(F)F)(=O)=O)=[O:28])([CH3:25])([CH3:24])[CH3:23]>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[C:43]([O:42][C:40]([N:39]=[C:30]([NH:29][C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])[NH:6][C:7]1[CH:11]=[N:10][N:9]2[CH2:12][CH2:13][NH:14][C:8]=12)=[O:41])([CH3:46])([CH3:45])[CH3:44]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 7-amino-2,3-dihydro-1H-imidazo[1,2-b]pyrazole sulfuric acid salt (4.4 g), 4-(dimethylamino)pyridine (244 mg) and triethylamine (8.10 g) in chloroform (45 ml) was added 1,3-bis(tert-butoxycarbonyl)-2-(trifluoromethanesulfonyl)guanidine (10.18 g). The mixture was stirred at room temperature for 2 hours. The reaction mixture was washed successively with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was triturated with diisopropyl ether to give 7-[2,3-bis(tert-butoxycarbonyl)guanidino]-2,3-dihydro-1H-imidazo[1,2-b]pyrazole (4.6 g) as a solid.
Workup
- washThe reaction mixture was washed successively with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogen carbonate solution
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was triturated with diisopropyl ether
Sources & evidence
- ORD record
- ord-218ff1fab34c4b89b5e50c45e0058e3c
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07129232B2
Reaction notes
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