Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 67460057 | HCID 67460057 | — |
| Reactant | 2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarbonyl chloride | HCID 86637727 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 66795948 | HCID 66795948 | 80.5% |
Reaction Steps
2-[1-[[5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarbonyl chloride (210 mg, 0.5 mmol) (i.e. the product of Example 19, Step D) was treated with a solution of (1R)-2,3-dihydro-N,2-dimethyl-1H-inden-1-amine (147 μL, 1.0 mmol) and triethylamine (139 μL, 1.0 mmol) in 5 mL of dichloromethane. The reaction mixture was stirred at room temperature for 2 h, passed through a Varian 1005 Chem Elut™ column pretreated with 3 mL of 1 N aqueous hydrochloric acid. The column was flushed with three column volumes of dichloromethane. The collected dichloromethane solution was evaporated in vacuo and purified by medium-pressure liquid chromatography on silica gel using 50-100% of ethyl acetate in 1-chlorobutane as eluant to give 214 mg of the title compound, the product of present invention as a white foam.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08586611B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-f3131614f15d4ba79f1d173981d0e7ce |
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| Source note | uspto-grants-2013_11 |
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