Diisopropylethylamine → 2-[4-(1-Isopropoxycarbonyl-piperidin-4-yloxyimino)-piperidin-1-yl]-4-trifluoromethyl-pyrimidine-5-carboxylic acid methyl ester

https://huagongshe.com/reaction/2066873

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate	HCID 3696469	—
Reactant	Isopropyl 4-(Piperidin-4-ylideneaminooxy)piperidine-1-carboxylate	HCID 57461147	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Solvent	Sodium Bicarbonate	HCID 516892	—
Product	2-[4-(1-Isopropoxycarbonyl-piperidin-4-yloxyimino)-piperidin-1-yl]-4-trifluoromethyl-pyrimidine-5-carboxylic acid methyl ester	HCID 86655015	—

Reaction Conditions

Temperature	110 °C

Reaction Steps

2-Chloro-4-trifluoromethyl-pyrimidine-5-carboxylic acid methyl ester (0.2 g, 0.78 mmol), 2d (0.2 g, 0.71 mmol), and diisopropylethylamine (0.2 mL, 1.2 mmol) were combined in 2 mL of DMSO and stirred at 110° C. for 18 h. The mixture was cooled to room temperature, diluted with aqueous NaHCO3 (5 mL) and extracted with EtOAc (5 mL). The organic layer was concentrated under vacuum to afford the crude 57a.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08293729B2
Source dataset	uspto-grants-2012_10
ORD ID	ord-7dcc7eafb69e42f88f640d1e25bf4937
Source note	uspto-grants-2012_10