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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2060618Generated: October 26, 2026

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

https://huagongshe.com/reaction/2060618

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-Methyl-2-butanolHCID 6405—
ReactantPotassium CarbonateHCID 11430—
Reactant2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 11155794—
Reactant5-Amino-2-[4-(1-hydroxy-1-methylethyl)phenyl]-1,3-thiazole-4-carboxamideHCID 58335264—
Reactant2-(6-Chloro-2-methylpyridin-3-yl)propan-2-olHCID 58335266—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
Product5-{[5-(1-Hydroxy-1-methylethyl)-6-methylpyridin-2-yl]amino}-2-[4-(1-hydroxy-1-methylethyl)phenyl]-1,3-thiazole-4-carboxamideHCID 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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08278335B2
Source datasetuspto-grants-2012_10
ORD IDord-21fe9570b4ef4f8282454986eb62990b
Source noteuspto-grants-2012_10