Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | P,P-Diphenylphosphinic azide | HCID 199401 | — |
| Reactant | Dimethyl-1,3-thiazole-5-carboxylic acid | HCID 736488 | — |
| Reactant | N-[5-(5-amino-6-chloropyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide | HCID 86244450 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86620403 | HCID 86620403 | 45% |
Reaction Steps
Diphenylphosphoryl azide (0.228 mL) was added to a stirred mixture of 2,4-dimethylthiazole-5-carboxylic acid (137 mg), triethylamine (0.148 mL) and toluene (3 mL) and the resultant mixture was heated to 100° C. for 1 hour. N-[5-(5-Amino-6-chloropyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide (100 mg) was added followed by 1,4-dioxane (3 mL) and the resultant solution was stirred and heated to 100° C. for 2 hours. The mixture was cooled to room temperature and concentrated by evaporation. The residue was purified by preparative HPLC. There was thus obtained the title compound as a white solid (69 mg, 45%); 1H NMR Spectrum: (DMSOd6) 2.16 (s, 3H), 2.27 (s, 3H), 2.39 (s, 3H), 2.54 (s, 3H), 8.17 (s, 1H), 8.65 (s, 1H), 8.82 (s, 1H), 9.75 (s, 1H); Mass Spectrum: M+H+ 437.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07868188B2 |
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| Source dataset | uspto-grants-2011_01 |
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| ORD ID | ord-e15d81bdbaa849f08fdd32ffafc74c8e |
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| Source note | uspto-grants-2011_01 |
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