Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | HCID 86670248 | HCID 86670248 | — |
| Reactant | HCID 178418573 | HCID 178418573 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 52919831 | HCID 52919831 | 4.24% |
Reaction Steps
(S)-ethyl 4-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl-carbamoyl)thiazole-2-carboxylate (0.755 g, 1.701 mmol) was dissolved in dry THF under nitrogen atmosphere. The solution was cooled to −78° C. with acetone-dry icebath. Methylmagnesium bromide, 3 M solution in Et2O (1.134 ml, 3.40 mmol), was added and the reaction mixture was stirred in RT. After the reaction was finished, saturated ammoniumchloride, water and DCM was added. The organic phase was washed with water. The product was purified with Flash-chromatography. Yield 4.24%. 1H-NMR (400 MHz; CDCl3): δ 1.28 (d, 3H), 1.65 (d, 6H), 3.00 (s, 1H), 4.35 (dd, 1H), 4.42 (dd, 1H), 4.58 (m, 1H), 6.62 (d, 7.50 (d, 1H), 7.66 (d, 1H), 7.67 (d, 1H), 7.80 (dd, 1H), 7.91 (d, 1H), 8.00 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08975254B2 |
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| Source dataset | uspto-grants-2015_03 |
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| ORD ID | ord-6eeab5fd0fe64896b14f2f5d0088eb0e |
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| Source note | uspto-grants-2015_03 |
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