HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 5-Methyl-thiazole-2-carboxylic acid {3-(3-styryl-1H-indazol-6-yloxy)-phenyl]-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone | HCID 6775 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 5-Methyl-1,3-thiazole-2-carboxylic acid | HCID 21877349 | — |
| Reactant | 3-(3-Styryl-4,5-dihydro-1H-indazol-6-yloxy)-phenylamine | HCID 69370420 | — |
| Reactant | 3-[1-(5-methyl-thiazole-2-carbonyl)-3-styryl-1H-indazol-6-yloxy]-phenyl amide | HCID 86759685 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-Methyl-thiazole-2-carboxylic acid {3-(3-styryl-1H-indazol-6-yloxy)-phenyl]-amide | HCID 86598540 | — |
Reaction Steps
3-(3-Styryl-4,5-dihydro-1H-indazol-6-yloxy)-phenylamine was converted to 5-methyl-thiazole-2-carboxylic acid (3-[1-(5-methyl-thiazole-2-carbonyl)-3-styryl-1H-indazol-6-yloxy]-phenyl amide by treatment with 5-methyl-thiazole-2-carboxylic acid and HATU (o-(2-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate) in DMF and analogous work-up, DDQ treatment and isolation to Example 4(a), step (iv) (50% yield): 1H NMR(DMSO-d6) δ 10.85 (s, 1H), 8.45 (d, 1H, J=9.8 Hz), 8.24 (m, 3H), 7.99-7.62 (m, 6H), 7547.34 (m, 5H), 6.96 (d, 1H, J=8.5 Hz), 2.64 (s, 3H), 2.54 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06884890B2 |
| Source dataset | uspto-grants-2005_04 |
| ORD ID | ord-ab85366e3b154d43b6871312a4cc8c44 |
| Source note | uspto-grants-2005_04 |