Benzoic acid, 3-amino-, methyl ester → HCID 56967243, compound

Participants

Role	Name	HCID	Charge
Reactant	Benzoic acid, 3-amino-, methyl ester	HCID 78274	—
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 78101879	HCID 78101879	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 56967243	HCID 56967243	10.6%

Reaction Steps

3-(4-Adamantan-1-yl-phenoxy)-acrylic acid (110.6 mg, 0.5 mmol), 3-aminobenzoic acid methyl ester (151.2 mg, 1.0 mmol) and HATU (143.8 mg, 0.75 mmol) were mixed in 5 ml of DMF, to which DIPEA (0.13 ml, 0.75 mmol) was added, followed by stirring for 12 hours at room temperature. The reaction mixture was extracted with ethylacetate and 10% HCl, thereafter the organic layer was washed with NaCl solution and water, dried over anhydrous MgSO4, and concentrated. The residue was purified by silcagel column chromatography (n-Hexane:EtOAc=10:1) to give the target compound as a white solid (21.5 mg, yield: 10.6%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08940936B2
Source dataset	uspto-grants-2015_01
ORD ID	ord-37ba330925264c2696e141aa51d1a6a5
Source note	uspto-grants-2015_01