Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | N-Methyl-1-(2-methylphenyl)methanamine | HCID 263103 | — |
| Reactant | 1-(4-fluoro-phenyl)-5-formyl-4-isopropyl-1H-pyrazole-3-carboxylic acid | HCID 24754974 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 24755126 | HCID 24755126 | 71.6% |
Reaction Steps
To a solution of 1-(4-fluoro-phenyl)-5-formyl-4-isopropyl-1H-pyrazole-3-carboxylic acid (1.50 g, 5.43 mmol) in CH2Cl2 (100 mL) at 25° C. was added EDCI (1.56 g, 8.14 mmol) followed by HOBt.H2O (1.25 g, 8.14 mmol) and the reaction was stirred for 10 min at 25° C. Subsequently, methyl-(2-methyl-benzyl)-amine (1.10 g, 8.14 mmol) was added and the reaction was stirred for an additional 6 hrs at 25° C. The organic layer was then washed with HCl, saturated NaHCO3 and brine. After drying over Na2SO4 and concentration, the product was purified by column chromatography (10-25 % EtOAc/Hex) to afford desired 1-(4-fluoro-phenyl)-5-formyl-4-isopropyl-1H-pyrazole-3-carboxylic acid methyl-(2-methyl-benzyl)-amide as an oil (1.53 g, 71.6%). MS(APCI+) 394.2 m/z (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07446121B2 |
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| Source dataset | uspto-grants-2008_11 |
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| ORD ID | ord-71b0966a354245b89ba0f29834941af0 |
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| Source note | uspto-grants-2008_11 |
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