Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Bromoethyl methyl ether | HCID 80972 | — |
| Reactant | HCID 67345762 | HCID 67345762 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 67348986 | HCID 67348986 | 50.7% |
Reaction Steps
To a DMF solution (1 mL) containing 5-[1-(4-Chloro-2-trifluoromethyl-benzyl)-1H-indazol-5-ylmethylene]-2-(methyl-piperidin-4-yl-amino)-thiazol-4-one (Example 16, 54 mg, 0.1 mmol) was added 1-bromo-2-methoxyethane (27.8 mg, 0.2 mmol) and K2CO3 (28 mg, 0.2 mmol). The mixture was stirred at 70° C. for 4 h, diluted with water and extracted with EtOAc. The combined EtOAc extracts were washed with brine, dried (Na2SO4), and evaporated. The residue was purified by flash column chromatography on silica gel (EtOAc→10% MeOH/EtOAc) to afford the desired product (30 mg, 50%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08426604B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-f407b267dc5e44bebda3b6a79e2af0cb |
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| Source note | uspto-grants-2013_04 |
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