Diisopropylethylamine → tert-butyl 5-((1H-pyrrole-3-carboxamido)methyl)-4,6-dimethylpyridin-2-ylcarbamate

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Pyrrole-3-carboxylic acid	HCID 101030	—
Reactant	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Reactant	N-[5-(aminomethyl)-4,6-dimethyl(2-pyridyl)] (tert-butoxy)carboxamide	HCID 22475372	—
Solvent	Dichloromethane	HCID 6344	—
Product	tert-butyl 5-((1H-pyrrole-3-carboxamido)methyl)-4,6-dimethylpyridin-2-ylcarbamate	HCID 58081282	—

Reaction Steps

To a mixture of 1H-pyrrole-3-carboxylic acid (1.40 g, 12.60 mmol), tert-butyl 5-(aminomethyl)-4,6-dimethylpyridin-2-ylcarbamate (3.48 g, 13.86 mmol) and DIPEA (6.60 ml, 37.8 mmol) in DCM (100 ml) was added HBTU (5.73 g, 15.12 mmol) at rt and was stirred at rt for 12 hours. The suspension was filtered off. The solid was washed with DCM and dried under reduced pressure to afford pure tert-butyl 5-((1H-pyrrole-3-carboxamido)methyl)-4,6-dimethylpyridin-2-ylcarbamate. HPLC (Method G) Rt=1.35 min; MS [M+H]+=345.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09290485B2
Source dataset	uspto-grants-2016_03
ORD ID	ord-0360d1c81acd4034b2ea1222bc6ade9f
Source note	uspto-grants-2016_03