Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | (Chloromethyl)cyclopropane | HCID 80013 | — |
| Reactant | 2,3-Dihydro-4-hydroxy-2,2-dimethyl-N-(1-methyl-1H-pyrazol-3-yl)-6-benzofurancarboxamide | HCID 59560084 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 59560283 | HCID 59560283 | — |
Reaction Steps
To 60 mg of cesium carbonate (180 μmol) in a test tube (10×95 mm) was added 0.8 mL of 0.1 M solution of 4-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carbo-xylic acid (1-methyl-1H-pyrazol-3-yl)-amide (31a) in acetonitrile followed by 1 mL of 0.1 M solution of chloromethyl cyclopropane in acetonitrile and the reaction was stirred at 80° C. for 8 h. After the removal of solid cesium carbonate, the acetonitrile was removed, the residue was reconstituted in 1.2 mL of DMSO and subjected to HPLC purification to obtain the title compound. 1H NMR (500 MHz, DMSO-d6) δ 10.56 (s, 1 H) 7.57 (s, 1 H) 6.92 (s, 1 H) 6.54 (s, 1 H) 3.92-3.93 (d, J=5.00 Hz, 2 H) 2.94 (s, 2 H) 1.42 (s, 6 H) 0.55-0.60 (m, 2 H) 0.30-0.35 (m, 1 H); LCMS for C19H23N3O3 m/z 342 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07842713B2 |
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| Source dataset | uspto-grants-2010_11 |
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| ORD ID | ord-16b564d3fdb14bb3a257effedf21f5ce |
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| Source note | uspto-grants-2010_11 |
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