Triethylamine → tert-Butyl 4-(4-isopropylthiazole-2-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-Thiazolecarboxylic acid, 4-(1-methylethyl)-	HCID 22499307	—
Reactant	tert-Butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate	HCID 53302318	—
Solvent	Dimethylformamide	HCID 6228	—
Product	tert-Butyl 4-(4-isopropylthiazole-2-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate	HCID 57988958	—

Reaction Steps

HATU (0.924 g) was added in one portion to a stirred solution at 0° C. of 4-isopropylthiazole-2-carboxylic acid (0.32 g) and tert-butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate (example 12, step b) (0.547 g) and triethylamine (0.781 mL) in DMF (12 mL). The reaction mixture was stirred at room temperature for 2 hours. 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 30% ethyl acetate in isohexane as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.54 g.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08148373B2
Source dataset	uspto-grants-2012_04
ORD ID	ord-b6cbd4888399410e950094bec0825b4c
Source note	uspto-grants-2012_04