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

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	(2-Thienylmethyl)amine	HCID 34005	—
Edukt	Diisopropylethylamine	HCID 81531	—
Edukt	2-Chloro-6-methylnicotinic acid	HCID 121724	—
Edukt	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Lösungsmittel	Dimethylformamide	HCID 6228	—
Lösungsmittel	Ethyl Acetate	HCID 8857	—
Lösungsmittel	Ethyl acetate hexane	HCID 21226206	—
Produkt	2-chloro-6-methyl-N-(thiophen-2-ylmethyl)nicotinamide	HCID 86628836	63%

Reaktionsbedingungen

Temperatur	0 °C

Reaktionsschritte

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.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US08084470B2
Quelldatensatz	uspto-grants-2011_12
ORD ID	ord-576134ea9a1c469596421bcd43466380
Quellennotiz	uspto-grants-2011_12