Dimethylformamide → (R)-2-bromo-N-(1-(3-methoxyphenyl)ethyl)thiazole-5-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-Bromothiazole-5-carboxylic acid	HCID 2763210	—
Reactant	(R)-1-(3-Methoxyphenyl)ethylamine	HCID 7020759	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Solvent	Water	HCID 962	—
Product	(R)-2-bromo-N-(1-(3-methoxyphenyl)ethyl)thiazole-5-carboxamide	HCID 68986687	—

Reaction Conditions

Temperature	50 °C

Reaction Steps

To a stirring solution of 2-bromothiazole-5-carboxylic acid (0.3 g, 1.442 mmol), diisopropyl ethylamine (0.205 g, 1.586 mmol) and HATU (0.603 g, 1.586 mmol) in dimethylformamide (7.21 mL, 1.442 mmol) was added (R)-1-(3-methoxyphenyl)ethanamine (0.218 g, 1.442 mmol) dropwise. After stirring for 12 hours at 50° C., the reaction was poured into water (50 mL). The precipitated solid was then collected by filtration washing successively with water (2×50 mL) and hexanes (2×50 mL). The recovered product was used without further purification in the next step.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09163007B2
Source dataset	uspto-grants-2015_10
ORD ID	ord-2b667a7780854547b398b7e4e2968f16
Source note	uspto-grants-2015_10