Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Azide | HCID 33557 | — |
| Reactant | HCID 86666731 | HCID 86666731 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86666732 | HCID 86666732 | 94% |
Reaction Steps
A mixture of (4-(3-(4-chlorobenzoyl)-1-methyl-1H-pyrazol-4-yl)-3-methylisoxazol-5-yl)methyl methanesulfonate (35 mg, 0.09 mmol), sodium azide (12 mg, 0.18 mmol) in N,N-dimethylformamide (10 mL) was heated to 80° C. and stirred for 10 h. After cooling to room temperature, the mixture was concentrated, and the residue was purified by flash chromatography eluting with petroleum ether/ethyl acetate=1:3 to give the titled product as a colorless oil (30 mg, 94%). LC/MS: m/z 356 [M+H]+; 1H NMR (300 MHz, CDCl3) δ 8.16 (d, J=9 Hz, 2H), 7.50 (s, 1H), 7.46 (d, J=9 Hz, 2H), 4.37 (s, 2H), 4.09 (s, 3H), 2.19 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08796261B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-4d8ab02439274190a3a700e275a826ab |
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| Source note | uspto-grants-2014_08 |
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