Triethylamine → 1,1-Dimethylethyl 10-[(2-methyl-4-thiazolyl)carbonyl]-7-oxa-3,10-diazaspiro[5.6]dodecane-3-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	2-Methyl-1,3-thiazole-4-carboxylic acid	HCID 284728	—
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	Tert-butyl 7-oxa-3,10-diazaspiro[5.6]dodecane-3-carboxylate	HCID 57989265	—
Solvent	Dimethylformamide	HCID 6228	—
Product	1,1-Dimethylethyl 10-[(2-methyl-4-thiazolyl)carbonyl]-7-oxa-3,10-diazaspiro[5.6]dodecane-3-carboxylate	HCID 57989321	—

Reaction Conditions

Temperature	20 °C

Reaction Steps

HATU (0.322 g) was added in one portion to a solution at 0° C. of tert-butyl 7-oxa-3,10-diazaspiro[5.6]dodecane-3-carboxylate (example 89, step e) (0.176 g) and 2-methylthiazole-4-carboxylic acid (0.093 g) and triethylamine (0.36 mL) in DMF (10 mL). The mixture was then stirred at 20° C. for 1 hour. The reaction 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 eluting with ethyl acetate. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 210 mg.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08629271B2
Source dataset	uspto-grants-2014_01
ORD ID	ord-07bc0f3917c047d791aa43f8924cf75e
Source note	uspto-grants-2014_01