Triethylamine → tert-Butyl 4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

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	2-(Propan-2-yl)-1,3-thiazole-4-carboxylic acid	HCID 22573065	—
Reactant	Tert-butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride	HCID 66964240	—
Solvent	Dimethylformamide	HCID 6228	—
Product	tert-Butyl 4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate	HCID 57989200	—

Reaction Conditions

Temperature	20 °C

Reaction Steps

A solution of 2-isopropylthiazole-4-carboxylic acid (1 g) and tert-butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride [WuXi PharmaTech] (1.71 g) in DMF (30 mL) was cooled in an ice bath and treated with triethylamine (2.44 mL) followed by HATU (2.89 g). The ice bath was removed and the mixture was stirred at 20° C. for 1 hour. The mixture was partitioned between ethyl acetate and brine, the organic layer was washed twice with brine, dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure. The crude product was purified by flash silica chromatography using 70% ethyl acetate in isohexane as solvent. Fractions containing the product were evaporated to dryness to afford the subtitled compound. Yield 2.0 g.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08455483B2
Source dataset	uspto-grants-2013_06
ORD ID	ord-e536f974dad9430199ca9f3d1d67675a
Source note	uspto-grants-2013_06