Triethylamine → 1-[(3,4-Dichlorophenyl)methyl]-5-methyl-N-(4-{[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]oxy}phenyl)-1H-1,2,3-triazole-4-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
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	4-[2-(Oxan-2-yloxy)ethoxy]aniline	HCID 11020917	—
Reactant	1-(3,4-dichlorobenzyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid	HCID 55029873	—
Solvent	Dimethylformamide	HCID 6228	—
Product	1-[(3,4-Dichlorophenyl)methyl]-5-methyl-N-(4-{[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]oxy}phenyl)-1H-1,2,3-triazole-4-carboxamide	HCID 59583419	—

Reaction Conditions

Temperature	45 °C

Reaction Steps

A mixture of 1-[(3,4-dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazole-4-carboxylic acid (Intermediate 11) (0.3 g, 1 mmol), 4-{[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]oxy}aniline (Intermediate 18) (0.28 g, 1.2 eq), HATU (0.8 g, 2 eq), and NEt3 (440 μL, 3 eq) in DMF was stirred at 45° C. for 18 hours. The solvent was evaporated and the residue was washed with water and extracted with a mixture of ether and ethyl acetate. The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The title compound was obtained and used in the next step without purification and isolation.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09051281B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-7d67dea4d950469cbbc3e480374383a3
Source note	uspto-grants-2015_06