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                            The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
 
                
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    							Batch number can be found on the product's label following the word 'Batch'.
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| CAS No. : | 128293-62-9 | 
| Formula : | C7H11N3O2 | 
| M.W : | 169.18 | 
| SMILES Code : | O=C(C1=NC(N)=CN1C)OCC | 
| MDL No. : | MFCD16036321 | 
| GHS Pictogram: |   | 
| Signal Word: | Warning | 
| Hazard Statements: | H302 | 
| Precautionary Statements: | P280-P305+P351+P338 | 
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 95% | With hydrogen;palladium 10% on activated carbon; In ethanol; ethyl acetate; under 836.056 Torr; for 3 - 4h; | Im-2 (0.4 g) in ETOH/ETHYL acetate (1: 1,14 mL) and Pd/C (10%, 0.3 g) were stirred under a slight positive pressure of hydrogen (ca 1.1 atm) for 3-4 hr. The reaction mixture was filtered using celite and solvent evaporated on the rotary. The remaining solid was freeze dried to yield a slightly yellow product. Yield (0.38 g, 95%). 1H NMR (DMSO): 8 6.45 (s, 1H), 4.5 (bs, 2H, NH2), 4.2 (q, 2H, J=7 Hz), 3.76 (s, 3H), 1.24 (t, 3H, J=7. 9 Hz). | 
| With 5%-palladium/activated carbon; hydrogen; In ethanol; at 20℃; for 12h; | Ethyl 1-methyl-4-nitroimidazole-2-carboxylate17 (6, 613 mg, 3.1 mmol) was hydrogenated over 5% palladium on charcoal in ethanol. The resulting amino compound was dried thoroughly under vacuum to remove traces of ethanol. It was then dissolved in dichloromethane (20.0 mL) and the solution was cooled to 0-5 C. To the cold solution was added triethylamine (0.5 mL, 3.7 mmol) followed by benzoyl chloride (0.4 mL, 3.4 mmol). The reaction mixture was allowed to attain room temperature and then stirred for 12 h. Upon completion, the reaction was quenched with water (15.0 mL) and stirred for 15 min. The organic layer was separated and aqueous layer was washed with dichloromethane (2 × 10 mL). Combined organic layers were dried over sodium sulfate and evaporated to obtain a yellow oil. The crude product was purified by column chromatography using silica gel and 2% methanol in chloroform as the eluent system to obtain 7 as a yellow solid (808 mg, 96%). | 
 [ 128293-62-9 ]
                                                    
                                                    [ 128293-62-9 ]
 [ 535937-85-0 ]
                                                    
                                                    [ 535937-85-0 ]
 [ 128293-62-9 ]
                                                    
                                                    [ 128293-62-9 ]
 [ 535937-82-7 ]
                                                    
                                                    [ 535937-82-7 ]
 [ 28920-43-6 ]
                                                    
                                                    [ 28920-43-6 ]
 [ 128293-62-9 ]
                                                    
                                                    [ 128293-62-9 ]

 [ 128293-62-9 ]
                                                    
                                                    [ 128293-62-9 ]
| Yield | Reaction Conditions | Operation in experiment | 
|---|---|---|
| 63% | The compound 7 was dissolved in methanol (94.4 ml), mixed with 10 % Pd/C (1.18 g) and stirred for four hours under hydrogen atmosphere. 10% Pd/C was removed from the reaction system with cerite filtration, so that the solvent was distilled out under a reduced pressure. Dimethylformamide (10 ml) was added to the residue and distilled out again under a reduced pressure. The residue was dissolved in dimethylformamide (10 mL) again, and mixed with the compound 8 (5. 9 g, 23.6mmol) (Baird, E. E. ; Dervan, P. B. J. Org. Chem. 1996, 118, 6141-6146), EDC (9.05 g, 47.2 mmol) and dimethylaminopyridine (288 mg, 2. 36 mmol), and stirred for 12 hours at a room temperature. Re-precipitation treatment with chloroform and ethyl acetate gave the compound 9 as white powder (5.9 g, 63%). 1HNMR(DMSO-d6) delta 1.28-1.30 (3H, t, J = 7.1 Hz), 3.85(3H, s), 3.93(3H, s), 3.98(3H, s), 4.25-4.29 (2H, dd, J = 7.1 Hz), 7.03(1H, d, J = 0.7 Hz), 7.22(1H, d, J = 2.0 Hz), 7.38(1H, s), 7.38(1H, s), 7.66(1H, s), 10.35(1H, s), 10.74(1H, s) ; 13CNMR(DMSO-d6) delta 14.3, 35.3, 35.7, 36.5, 60.8, 106.4, 115.6, 119.8, 121.6, 122.2, 126.5, 127.2, 131.0, 138.0, 139.0, 156.3, 158.7, 158.9: Anal. Calcd. for C18H12N4O3·H2O: C, 53.22; H, 4.89; N, 22.57. Found: C, 50.88; H,4.88; N,23.13. | 
 [ 128293-62-9 ]
                                                    
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 [ 128293-62-9 ]
                                                    
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