HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Methyl-2-butanol → 5-{[5-(1-Hydroxy-1-methylethyl)-6-methylpyridin-2-yl]amino}-2-[4-(1-hydroxy-1-methylethyl)phenyl]-1,3-thiazole-4-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Methyl-2-butanol | HCID 6405 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Reactant | 5-Amino-2-[4-(1-hydroxy-1-methylethyl)phenyl]-1,3-thiazole-4-carboxamide | HCID 58335264 | — |
| Reactant | 2-(6-Chloro-2-methylpyridin-3-yl)propan-2-ol | HCID 58335266 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Product | 5-{[5-(1-Hydroxy-1-methylethyl)-6-methylpyridin-2-yl]amino}-2-[4-(1-hydroxy-1-methylethyl)phenyl]-1,3-thiazole-4-carboxamide | HCID 57482803 | — |
Reaction Steps
The title compound was prepared as described in Example 1, Step 2 using 5-amino-2-[4-(1-hydroxy-1-methylethyl)phenyl]-1,3-thiazole-4-carboxamide (Example 5, Step 3) (150 mg, 0.54 mmol), 2-(6-chloro-2-methylpyridin-3-yl)propan-2-ol (100 mg, 0.54 mmol), Pd2(dba)3 (30 mg, 0.032 mmol), X-PHOS (77 mg, 0.16 mmol), potassium carbonate (82 mg, 0.60 mmol), and tert-amyl alcohol (1.1 ml) as starting materials. 1H NMR (500 MHz, d6-DMSO) δ 11.17 (s, 1H), 7.87 (d, 2H), 7.34 (d, 1H), 7.69 (s, 1H), 7.58 (s, 1H), 7.55 (d, 2H), 6.95 (d, 1H), 5.11 (s, 1H), 5.02 (s, 1H), 2.76 (s, 3H), 1.49 (s, 6H), 1.44 (s, 6H). LRMS (APCI) calc'd for C22H27N4O3S [M+H]+ 427.2, found 427.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08278335B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-21fe9570b4ef4f8282454986eb62990b |
| Source note | uspto-grants-2012_10 |