(2-Thienylmethyl)amine → 2-chloro-6-methyl-N-(thiophen-2-ylmethyl)nicotinamide

Participants

Role	Name	HCID	Charge
Reactant	(2-Thienylmethyl)amine	HCID 34005	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-Chloro-6-methylnicotinic acid	HCID 121724	—
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	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	Ethyl acetate hexane	HCID 21226206	—
Product	2-chloro-6-methyl-N-(thiophen-2-ylmethyl)nicotinamide	HCID 86628836	63%

Reaction Conditions

Temperature	0 °C

Reaction Steps

2.67 g (7.0 mmol) of HATU and 4.0 ml (23.2 mmol) of DIPEA were added at 0° C. to a solution of 1.0 g (5.8 mmol) of 2-chloro-6-methyl-nicotinic acid in DMF (20 ml), and the mixture was stirred for 20 min at 0° C. At that temperature, 656 mg (5.8 mmol) of thiophen-2-ylmethylamine were added. Stirring was then carried out for 16 h at RT. The mixture was then diluted with EA and washed in succession with sat. aq. NaHCO3 solution and brine. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. CC (hexane/EA 4:1) of the residue yielded 966 mg (3.6 mmol, 63%) of 2-chloro-6-methyl-N-(thiophen-2-ylmethyl)nicotinamide.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08084470B2
Source dataset	uspto-grants-2011_12
ORD ID	ord-576134ea9a1c469596421bcd43466380
Source note	uspto-grants-2011_12