HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 5-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid ((-)-methylcarbamoyl-phenyl-methyl)-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | (2R)-2-amino-N-methyl-2-phenylacetamide hydrochloride | HCID 71087301 | — |
| Reactant | 5-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid | HCID 71087346 | — |
| Solvent | Heptane | HCID 8900 | — |
| Product | 5-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid ((-)-methylcarbamoyl-phenyl-methyl)-amide | HCID 78012188 | — |
Reaction Steps
The title compound was synthesized in analogy to Example 1, using 5-cyclopropyl-6-cyclopropylmethyloxy-pyridine-2-carboxylic acid (Example 42 a) and (αR)-α-amino-N-methyl-benzeneacetamide hydrochloride (1:1) (CAN 97549-10-5) as starting materials. Racemization occurred during the synthesis and the product was isolated by chiral chromatography on Chiralpak AD using heptane/20% ethanol as eluent. The (−)-enantiomer was isolated. LC-MS (UV peak area/ESI) 100%, 380.1968 (M+H)+, αD20 (MeOH)=−6.0°.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09321727B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-25ce21494def4c18b2cf5d3ae444db82 |
| Source note | uspto-grants-2016_04 |