3,4-Dimethoxyaniline → HCID 25265258, compound

Participants

Role	Name	HCID	Charge
Reactant	3,4-Dimethoxyaniline	HCID 22770	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1-[(4-Fluorophenyl)methyl]-5-methyl-1H-1,2,3-triazole-4-carboxylic acid, 4-Carboxy-1-(4-fluorobenzyl)-5-methyl-1H-1,2,3-triazole	HCID 2764581	—
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	Dimethylformamide	HCID 6228	—
Product	HCID 25265258	HCID 25265258	—

Reaction Steps

A mixture of 1-[(4-fluorophenyl)methyl]-5-methyl-1H-1,2,3-triazole-4-carboxylic acid (0.2 g, 0.85 mmol), 3,4-bis(methyloxy)aniline (0.156 g, 1.2 eq), HATU (0.485 g, 1.5 eq) and DIPEA (240 μL, 1.5 eq) in DMF was stirred at room temperature overnight. The solvent was evaporated and the residue was washed with water and extracted with DCM. The organic phase was dried over sodium sulphate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography eluting with DCM to give after precipitation from ether, the title compound as a white solid (180 mg, 57%). HRMS calculated for C19H19FN4O3 (M+H)+371.1519. found: 371.1500, Rt: 2.78 min. MP: 119.7° C.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09051281B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-cabebb7dda4f45098103f8726be85380
Source note	uspto-grants-2015_06