Diisopropylethylamine → 2-(2-Isobutyryl-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

Participants

Role	Name	HCID	Charge
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	—
Reactant	2-Isobutyryl-3-methyl-benzoic acid	HCID 59314181	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-(2-Isobutyryl-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester	HCID 59314272	89.1%

Reaction Steps

To a solution of 2-isobutyryl-3-methyl-benzoic acid (227) (200 mg, 0.97 mmol), 2-amino-indan-2-carboxylic acid ethyl ester (220 mg, 1.07 mmol), HATU (441 mg, 1.16 mmol) in anhydrous DMF (10 mL) is added DIPEA (192 μL, 1.16 mmol). The resulting solution is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in DCM (50 mL) and washed with water (1×5 mL) and brine (1×5 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by HPLC to give a pure product (228) as a pale yellow solid (340 mg, 89%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08569535B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-1845e479517e4873bf29498329093dfe
Source note	uspto-grants-2013_10