Diisopropylethylamine → [5-({[1-(4-Hydroxymethyl-benzyl)-1H-[1,2,3]triazole-4-carbonyl]-amino}-methyl)-4,6-dimethyl-pyridin-2-yl]-carbamic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	N-[5-(aminomethyl)-4,6-dimethyl(2-pyridyl)] (tert-butoxy)carboxamide	HCID 22475372	—
Reactant	1-(4-Hydroxymethyl-benzyl)-1H-[1,2,3]triazole-4-carboxylic acid	HCID 58081318	—
Solvent	Dimethylformamide	HCID 6228	—
Product	[5-({[1-(4-Hydroxymethyl-benzyl)-1H-[1,2,3]triazole-4-carbonyl]-amino}-methyl)-4,6-dimethyl-pyridin-2-yl]-carbamic acid tert-butyl ester	HCID 58081262	—

Reaction Steps

A mixture of 1-(4-hydroxymethyl-benzyl)-1H-[1,2,3]triazole-4-carboxylic acid (0.95 g, 4.07 mmol), (5-Aminomethyl-4,6-dimethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (1.024 g, 4.07 mmol), HATU (2.013 g, 5.30 mmol) and DIPEA (2.85 mL, 16.29 mmol) in 50 mL DMF was stirred at room temperature for 3 h. The reaction mixture was concentrated under reduced pressure. The residue was taken up in ethyl acetate and washed with 1 n HCl solution and saturated sodium bicarbonate solution. The organic solution was dried over MgSO4, filtered and concentrated to yield the crude product which was used in the next step without further purification. LCMS (Method A) RtA=1.279; [M+H]+=467.0.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09290485B2
Source dataset	uspto-grants-2016_03
ORD ID	ord-9f61457ea26d4292830f4617b48fa8f6
Source note	uspto-grants-2016_03