Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Trifluoroacetic anhydride | HCID 9845 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 136348384 | HCID 136348384 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 136348383 | HCID 136348383 | 52.6% |
Reaction Steps
[step 2] (E)-2-cyclopropyl-3-({3-fluoro-11(6H)-[1-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)ethylidene]dibenzo[b,e]oxepin-8-yl}methyl)imidazo[1,2-a]pyridine-7-carboxamide (83 mg, 0.15 mmol) obtained in step 1 was suspended in THF (0.77 mL), and triethylamine (0.11 mL, 0.77 mmol) was added. Under ice-cooling, trifluoroacetic anhydride (0.11 mL, 0.77 mmol) was added, and the mixture was stirred at room temperature for 4 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the mixture, and the mixture was extracted 3 times with chloroform-methanol mixed solvent. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=100/0 v/v-90/10 v/v) to give the title compound (compound 14b) (41 mg, 51%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08969345B2 |
|---|
| Source dataset | uspto-grants-2015_03 |
|---|
| ORD ID | ord-f063c3b15d854660b821e67a3540b124 |
|---|
| Source note | uspto-grants-2015_03 |
|---|