HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Methyl-2-butanol → 2-[4-(1-Hydroxy-1-methylethyl)phenyl]-5-{[5-(methylsulfonyl)pyridin-2-yl]amino}-1,3-thiazole-4-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Methyl-2-butanol | HCID 6405 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Bromo-5-(methylsulfonyl)pyridine | HCID 9899483 | — |
| 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 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Product | 2-[4-(1-Hydroxy-1-methylethyl)phenyl]-5-{[5-(methylsulfonyl)pyridin-2-yl]amino}-1,3-thiazole-4-carboxamide | HCID 44623044 | — |
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-bromo-5-(methylsulfonyl)pyridine (128 mg, 0.54 mmol), Pd2(dba)3 (30 mg, 0.032 mmol), X-PHOS (77 mg, 0.16 mmol), potassium carbonate (75 mg, 0.54 mmol), and tert-amyl alcohol (1.1 ml) as starting materials. 1H NMR (500 MHz, d6-DMSO) δ 11.72 (s, 1H), 8.79 (d, 1H), 8.13 (dd, 1H), 7.91 (m, 3H), 7.79 (s, 1H), 7.57 (d, 2H), 7.44 (d, 1H), 5.74 (s, 1H), 3.26 (s, 3H), 1.44 (s, 6H). LRMS (APCI) calcd for C19H21N4O4S2 [M+H]+ 433.1, found 433.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08278335B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-1d205228d42d4607b7d7215a2a97ae17 |
| Source note | uspto-grants-2012_10 |