Diisopropylethylamine → 2,6-Dichloro-N-[2-(4-morpholinyl)ethyl]-4-pyridinecarboxamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2,6-Dichloroisonicotinic acid	HCID 94830	—
Reactant	HOAt	HCID 181649	—
Reactant	2-Morpholinoethylamine	HCID 408285	—
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	Dimethylacetamide	HCID 31374	—
Product	2,6-Dichloro-N-[2-(4-morpholinyl)ethyl]-4-pyridinecarboxamide	HCID 43235869	105%

Reaction Steps

HATU (989 mg, 2.6 mmol), HOAT (354 mg, 2.6 mmol) and DIEA (907 μl, 5.21 mmol) were added to a stirred solution of 2,6-dichloroisonicotinic acid (500 mg, 2.60 mmol) in anhydrous DMA (4 ml). The mixture was stirred for 10 minutes after which 2-morpholin-4-yl-ethylamine (420 μl, 2.86 mmol) was added. The mixture was stirred at room temperature for 12 h and the mixture was partitioned between EtOAc and water. The EtOAc layer was washed well with water, dried over sodium sulphate and concentrated in vacuo to give the title compound as an oil (830 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07709503B2
Source dataset	uspto-grants-2010_05
ORD ID	ord-4ab605f0abae4b7d852e4c8e1465e2fa
Source note	uspto-grants-2010_05