Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 2-(3-Methoxyphenoxy)acetamide | HCID 22115808 | — |
| Reactant | N-(3-fluoro-4-morpholinophenyl)-3-oxobutanamide | HCID 90023295 | — |
| Catalyst | Titanium isopropoxide | HCID 11026 | — |
| Solvent | O-Xylene | HCID 7237 | — |
| Product | HCID 90023036 | HCID 90023036 | 40.2% |
Reaction Steps
A mixture of N-(3-fluoro-4-morpholinophenyl)-3-oxobutanamide (1.0 g, 3.57 mmol), 2-(3-methoxyphenoxy)acetamide (1.29 g, 7.12 mmol) and titanium tetraisopropanolate (8.11 g, 28.5 mmol) in xylene (30 mL) was stirred at 165° C. for 24 h. The mixture was cooled to rt and 80 mL of toluene and 100 mL of saturated NH4Cl aqueous solution were added. The resulting mixture was stirred at rt overnight and filtered and the filtrate was extracted with DCM (150 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a yellow solid (0.61 g, 40%). The compound was characterized by the following spectroscopic data:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09434695B2 |
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| Source dataset | uspto-grants-2016_09 |
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| ORD ID | ord-dff102b59afc41608a8915c1af4d3654 |
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| Source note | uspto-grants-2016_09 |
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