Diisopropylethylamine → Methyl 2-(4-(tert-butoxycarbonyl)piperazin-1-yl)thiazole-4-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	tert-Butyl piperazine-1-carboxylate	HCID 143452	—
Reactant	Methyl 2-chloro-4-thiazolecarboxylate	HCID 7213135	—
Solvent	Dimethylacetamide	HCID 31374	—
Product	Methyl 2-(4-(tert-butoxycarbonyl)piperazin-1-yl)thiazole-4-carboxylate	HCID 89873086	35.1%

Reaction Conditions

Temperature	150 °C

Reaction Steps

Methyl 2-chlorothiazole-4-carboxylate (500 mg, 2.82 mmol), N-Boc-piperazine (655 mg, 3.52 mmol) and DIPEA (736 uL, 4.22 mmol) were dissolved in DMA (10 mL) and the reaction mixture was heated in a microwave reactor at 150° C. for 45 min. The reaction mixture was partitioned between EtOAc (40 mL) and water (40 mL) and the organic fraction was washed with water (40 mL) and brine (40 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography to give the title compound as a white solid (324 mg, 35.1%). LCMS (ES+): 350.1 [MNa]+. HPLC: Rt 6.04 min, 100% purity.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09428498B2
Source dataset	uspto-grants-2016_08
ORD ID	ord-a76bb42cf1ee4014bcbab54d8eb8113a
Source note	uspto-grants-2016_08