2-Aminoindane → Methyl 7-(4-((2,3-dihydro-1H-inden-2-yl)carbamoyl)phenoxy)-6-cyano-3,4-dihydro-2H-chromene-4-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	2-Aminoindane	HCID 76310	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Reactant	4-(6-Cyano-4-(methoxycarbonyl)-chroman-7-yloxy)benzoic acid	HCID 46221108	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	Methyl 7-(4-((2,3-dihydro-1H-inden-2-yl)carbamoyl)phenoxy)-6-cyano-3,4-dihydro-2H-chromene-4-carboxylate	HCID 67080302	75.3%

Reaction Steps

4-(6-Cyano-4-(methoxycarbonyl)chroman-7-yloxy)benzoic acid (from Example 7, Step B) (12 mg, 0.034 mmol), HBTU (15 mg, 0.041 mmol) were diluted with N-methylpyrrolidone (1 mL) followed by the addition of 2-aminoindan (4.5 mg, 0.034 mmol), N,N-diisopropylethylamine (0.015 mL, 0.085 mmol) and DMAP (1.2 mg, 0.010 mmol). After stirring for 3 hours, the reaction was loaded directly onto a Biotage 12i cartridge eluting with 5% ethyl acetate/hexanes to 100% ethyl acetate to yield the title compound (12 mg, 75% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08716498B2
Source dataset	uspto-grants-2014_05
ORD ID	ord-b8cf2d69d4184d21903af30b2763c99c
Source note	uspto-grants-2014_05