2-Aminothiazole → 2-(4-Cyclopropylsulfonylphenyl)-2-tetrahydropyran-4-yloxy-N-thiazol-2-yl-acetamide

Participants

Role	Name	HCID	Charge
Reactant	2-Aminothiazole	HCID 2155	—
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	(4-Cyclopropanesulfonyl-phenyl)-[(tetrahydro-pyran-4-yloxy)]-acetic acid	HCID 59610020	—
Solvent	Water	HCID 962	—
Solvent	Dichloromethane	HCID 6344	—
Product	2-(4-Cyclopropylsulfonylphenyl)-2-tetrahydropyran-4-yloxy-N-thiazol-2-yl-acetamide	HCID 88861763	48.2%

Reaction Steps

To a mixture of 2-(4-cyclopropylsulfonylphenyl)-2-tetrahydropyran-4-yloxy-acetic acid (preparation 4; 0.2 g, 0.58 mmol), 2-aminothiazole (0.070 g, 0.70 mmol), HOBt (0.095 g), and EDCl (0.134 g, 0.70 mmol) in methylene chloride (6 mL), was added N-methyl morpholine (0.08 mL, 0.70 mmol). The resulting mixture was stirred at room temperature overnight followed by dilution with methylene chloride. The reaction mixture was poured into water; organic layer was washed with water, brine, dried over sodium sulfate, and the organic solvent evaporated to get a residue which was purified by preparative TLC to obtain a title compound (0.118 g)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09340506B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-1e5bce55eb0543f4a1162636caa28399
Source note	uspto-grants-2016_05