HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 5-Bromo-6-chloro-N-((R)-1-hydroxymethyl-3-methyl-butyl)-nicotinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-Bromo-6-chloropyridine-3-carboxylic acid | HCID 285433 | — |
| Reactant | D(-)-Leucinol | HCID 2724002 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | 5-Bromo-6-chloro-N-((R)-1-hydroxymethyl-3-methyl-butyl)-nicotinamide | HCID 86619568 | 91.6% |
Reaction Steps
5-Bromo-6-chloro-nicotinic acid (2.0 g, 8.46 mmol) was dissolved in DMA (20 mL). To the solution was added TBTU (3.1 g, 9.3 mmol), N,N-diisopropylethyl amine (7.4 mL, 42 mmol) and (D)-leucinol (1.1 g, 9.3 mmol). The reaction mixture was stirred for 16 h at room temperature. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica (cyclohexane/ethyl acetate gradient) to yield 2.6 g of the title compound as a yellow oil, MS (ISP) 337.1 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08188093B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-806af77ff0d043719767746e063b44bd |
| Source note | uspto-grants-2012_05 |