Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | N,O-Dimethylhydroxylamine | HCID 14232 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | HCID 86668506 | HCID 86668506 | — |
| Solvent | Dimethylhydroxylamine | HCID 27970 | — |
| Product | HCID 60141904 | HCID 60141904 | — |
Reaction Steps
To a solution of 10.8 g (22.2 mmol) 3-(2-chloro-6-fluorophenyl)-5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylic acid, 2.17 g (1 eq) N,O-Dimethylhydroxylamine and 8.42 g (1 eq) HBTU in dimethylhydroxylamine 3.68 mL DIPEA were added. The mixture was stirred overnight at r.t. The solvent was removed in the vacuum. The residue was resolved in ethylacetate and extracted with sodium hydrogen carbonate (5%, aq) and citric acid (5%, aq). The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed in the vacuum. TLC (6:4 petrolether:ethylacetate) showed residual educt. The product was isolated by column chromatoghraphy (6:4) petrolether:ethylacetate). The product (example 63) was dried under vacuum to yield 2.28 g (19%). Result of LC/MS MH+: 528.8; 1H NMR (DMSO-d6; CCl4): 3.08 (3H, s, CH3), 3.36 (3H, s, CH3), 7.40-7.81 (7H, m, CH-arom.), 8.39 (1H, s, CH-pyraz.)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08592456B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-191818433fa84695bbae671d36c3b6d2 |
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| Source note | uspto-grants-2013_11 |
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