Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | N-Methylacetamide | HCID 6582 | — |
| Reactant | 2,6-Lutidine | HCID 7937 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 86678206 | HCID 86678206 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 71294469 | HCID 71294469 | 99% |
Reaction Steps
N-methylacetamide (0.097 mL, 1.30 mmol) was dissolved in dichloromethane (1.0 mL). To the solution were added at 0° C. 2,6-lutidine (0.30 mL, 2.5 mmol) and oxalyl dichloride (0.11 mL, 1.30 mmol). After stirring at the same temperature for 15 minutes, a solution of Compound B4 (145 mg, 0.253 mmol) obtained in Step 1 of Example 42 in dichloromethane (1.0 mL) was added and the mixture was further stirred at room temperature for 18 hours. A saturated aqueous sodium bicarbonate solution and water were added to the reaction mixture. Extraction with ethyl acetate and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=1/10) to give Compound B7 (157 mg, 99% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09150569B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-7eea97ee6b0b47cea3e22d1b3c6fa20e |
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| Source note | uspto-grants-2015_10 |
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