3,4,5-Trimethoxyaniline → HCID 59680037, compound

Participants

Role	Name	HCID	Charge
Reactant	3,4,5-Trimethoxyaniline	HCID 32285	—
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	HCID 11536035	HCID 11536035	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 59680037	HCID 59680037	—

Reaction Steps

For amide formation, 3-(oxazolo[4,5-b]pyridin-2-yl)benzoic acid (30 mg, 0.125 mmol) was dissolved in 2 mL of DMF along with 3,4,5-trimethoxyaniline (23 mg, 1 eq) and 71 mg of HATU (1.5 eq). After 45 microliters of DIEA (2 eq) were added, the reaction mixture was stirred at room temperature for 18 hrs. It was then diluted with ethyl acetate and washed with water and concentrated. The resulting residue was purified by chromatography using a 9:1 mixture of CH2Cl2 to MeOH to afford 3-(oxazolo[4,5-b]pyridin-2-yl)-N-(3,4,5-trimethoxyphenyl)benzamide. (MS, M++H=406).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08044198B2
Source dataset	uspto-grants-2011_10
ORD ID	ord-199082fa293e47f6b078205509dab340
Source note	uspto-grants-2011_10