Triethylamine → US10195181, Example 25a

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
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	4-amino-2-cyclohexyl-1,5-dimethyl-2,3-dihydro-1H-pyrazol-3-one	HCID 61273021	—
Reactant	Potassium 5-(4-(tert-butyl)-1,3-dioxolan-2-yl)-4-methylisoxazole-3-carboxylate	HCID 118511106	—
Solvent	Water	HCID 962	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	US10195181, Example 25a	HCID 118511076	—

Reaction Steps

To a solution of potassium 5-(4-(tert-butyl)-1,3-dioxolan-2-yl)-4-methylisoxazole-3-carboxylate (43.5 mg, 0.148 mmol) in NMP (0.7 mL) was added HATU (62.0 mg, 0.163 mmol), triethylamine (45.5 μl, 0.326 mmol) and 4-amino-2-cyclohexyl-1,5-dimethyl-1H-pyrazol-3(2H)-one (Intermediate D) (31.0 mg, 0.148 mmol) and the reaction mixture was stirred at room temperature overnight. To the resulting mixture was added water and EtOAc. The organics were washed with brine (×2), dried over MgSO4, filtered and the solvent removed under reduced pressure. The crude material was adsorbed onto silica and purification by chromatography eluting with 0-100% EtOAc in iso-hexane afforded the title compound as a mixture of diastereoisomers.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09403810B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-f51da8b4363c4845a6c90ae25a65b3d4
Source note	uspto-grants-2016_08