Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | O-Methylhydroxylamine hydrochloride | HCID 521874 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 67958233 | HCID 67958233 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86707231 | HCID 86707231 | — |
Reaction Steps
1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (663 mg, 3.46 mmol) and Et3N (0.900 ml, 6.46 mmol) were successively added to a solution of 3-[2-(2H-indazol-2-yl)nicotinamido]-2-hydroxy-4-phenylbutanoic acid (1200 mg, 2.88 mmol) and O-methylhydroxylamine hydrochloride (0.350 ml, 4.61 mmol) in DMF (35 ml) at 5° C., and the mixture was stirred for 5 minutes. A pH of 10 was adjusted by adding Et3N (0.643 ml, 4.61 mmol), stirring was continued for 1 hour at 5° C. and then overnight at room temperature. The reaction mixture was then concentrated under reduced pressure. To the obtained residue were added water (150 ml) and a saturated aqueous solution of NaHCO3 (20 ml) with stirring. Following stirring for about 20 minutes the precipitate formed was filtered off with suction and treated with methyl-tert.-butylether (40 ml) to give, after filtration and drying in vacuo, 1.07 g of the title compound as an off-white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09062027B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-d2467fbd95c74c7f8db5b8bb98cda7aa |
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| Source note | uspto-grants-2015_06 |
|---|