HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 5-Chloro-4-cyclobutylmethoxy-pyridine-2-carboxylic acid ((R)-1-hydroxymethyl-1,2-dimethyl-propyl)-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | R-2-Amino-2,3-dimethyl-butan-1-OL | HCID 12113027 | — |
| Reactant | 5-Chloro-4-cyclobutylmethoxy-pyridine-2-carboxylic acid | HCID 90203650 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 5-Chloro-4-cyclobutylmethoxy-pyridine-2-carboxylic acid ((R)-1-hydroxymethyl-1,2-dimethyl-propyl)-amide | HCID 76282484 | — |
Reaction Steps
To a solution of 5-chloro-4-cyclobutylmethoxy-pyridine-2-carboxylic acid (60 mg, 249 μmol) in acetonitrile (2 mL) was added HATU (123 mg, 324 μmol), (2R)-2-amino-2,3-dimethyl-1-butanol (CAN 155158-75-1, 32.1 mg, 274 μmol) and DIEA (217 μL, 1.25 mmol). The brownish reaction mixture was stirred for 18 h at room temperature. The crude reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography (silica, heptane/ethyl acetate gradient) and finally chiral chromatography (ChiralPak AD, heptane/ethanol 9:1) to deliver the desired compound (27.3 mg, 43%) as colorless oil. MS (ESI, m/z): 341.1 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09409866B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-6f117c21c45b45b78d1a40ac35841894 |
| Source note | uspto-grants-2016_08 |