2,3-Dihydro-1,4-benzodioxin-5-carboxylic acid → HCID 59314137, compound

Participants

Role	Name	HCID	Charge
Reactant	2,3-Dihydro-1,4-benzodioxin-5-carboxylic acid	HCID 78184	—
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	Ethyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate	HCID 10921653	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 59314137	HCID 59314137	91%

Reaction Steps

To a solution of 2,3-dihydro-benzo[1,4]dioxine-5-carboxylic acid (351 mg, 1.95 mmol), 2-amino-indan-2-carboxylic acid ethyl ester (400 mg, 1.95 mmol), HATU (1.11 g, 2.93 mmol) in anhydrous DMF (8 mL) is added DIPEA (484 μL, 2.93 mmol). The resulting solution is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (70 mL) and washed with water (1×10 mL) and brine (2×10 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by HPLC to give a pure product (59) as white solid (650 mg, 91%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08569535B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-9444d031c8854b31b93c0a88a9349f24
Source note	uspto-grants-2013_10