HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → N-(1H-Benzimidazol-6-ylmethyl)-2-[3-({[(2R)-1-isobutylpyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | (1H-Benzo[D]imidazol-5-YL)methanamine | HCID 11593548 | — |
| Reactant | 2-[3-({[(2R)-1-isobutylpyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid | HCID 59900536 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Ammonia | HCID 222 | — |
| Product | N-(1H-Benzimidazol-6-ylmethyl)-2-[3-({[(2R)-1-isobutylpyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetamide | HCID 59900495 | 11.1% |
Reaction Steps
HOBT (25 mg, 0.19 mmol), WSCDl.HCl (31 mg, 0.16 mmol), N-methylmorpholine (41 ml, 0.37 mmol) and 1H-benzimidazol-6-ylmethylamine (21 mg, 0.14 mmol) were added to a solution of 2-[3-({[(2R)-1-isobutylpyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid (preparation 62) (40 mg, 0.12 mmol) in N,N-dimethylformamide (2 ml), and the reaction was stirred at room temperature overnight. The mixture was evaporated under reduced pressure and the residue preadsorbed on to silica gel, and then purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (95:5:0.5) as eluant to provide the title compound (6 mg, 10%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06417203B1 |
| Source dataset | uspto-grants-2002_07 |
| ORD ID | ord-80bf60b5781c4477b326c895971d9c00 |
| Source note | uspto-grants-2002_07 |