Triethylamine → 5-Chloro-n-(4,4-dimethyl-6,7-dihydro-4h-pyrano[4,3-d]thiazol-2-yl)-2-methoxybenzamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	5-Chloro-o-anisic acid	HCID 76970	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	4,4-dimethyl-4H,6H,7H-pyrano[4,3-d][1,3]thiazol-2-amine	HCID 87179372	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Sodium Bicarbonate	HCID 516892	—
Product	5-Chloro-n-(4,4-dimethyl-6,7-dihydro-4h-pyrano[4,3-d]thiazol-2-yl)-2-methoxybenzamide	HCID 87179584	78.4%

Reaction Steps

To a solution of Example 89E (1.0 g, 5.6 mmol) in THF (30 mL) were added 5-chloro-2-methoxy-benzoic acid (1.86 g, 10.0 mmol, Aldrich), N-(3-dimethylaminopropyl)-N-ethylcarbodimide hydrochloride (1.91 g, 10.0 mmol, Aldrich), 1-hydroxybenzotriazole (1.35 g, 10.0 mmol) and triethylamine (3.5 mL, 3.5 mmol, Aldrich). The mixture was stirred overnight at room temperature. The reaction mixture was then diluted with 1 M aqueous NaHCO3 (20 mL) and the aqueous layer was extracted with ethyl acetate (2×30 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography (SiO2, 0-5% methanol in dichloromethane to afford 1.55 g (78%) of the title compound. MS (ESI+) m/z 353 (M+H)+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08865753B2
Source dataset	uspto-grants-2014_10
ORD ID	ord-0438e9ce93cf42c4881aa604fb5fdf3d
Source note	uspto-grants-2014_10