Triethylamine → N-(6-Chloro-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-4-yl)-3-(1-naphthyl)-propanamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	2-(Naphthalen-1-yl)propanoic acid	HCID 122752	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-amine	HCID 15338705	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-(6-Chloro-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-4-yl)-3-(1-naphthyl)-propanamide	HCID 44133803	—

Reaction Steps

The title compound was prepared from Intermediate 2 (200 mg, 0.896 mmol) and 1-naphthylpropanoic acid (178 mg, 0.896 mmol) in presence of EDCI.HCl (256 mg, 1.345 mmol), HOBt (205 mg, 1.345 mmol) and triethylamine (371 μl, 2.690 mmol) in dichloromethane (10 ml) as described in Example 1 to give 160 mg of the product as a white solid; 1H NMR (300 MHz, CDCl3) δ 1.43-1.51 (m, 1H), 1.63-1.69 (m, 1H), 1.81-1.97 (m, 2H), 2.09-2.26 (m, 4H), 2.64-2.70 (m, 2H), 3.50 (t, J=7.2 Hz, 2H), 5.14 (q, J=9.9 Hz, 1H), 5.26 (d, J=8.4 Hz, 1H), 6.65 (d, J=8.7 Hz, 1H), 6.82 (s, 1H), 7.01 (dd, J=2.4, 8.7 Hz, 1H), 7.35-7.54 (m, 4H), 7.73 (d, J=6.9 Hz, 1H), 7.84 (d, J=7.5 Hz, 1H), 8.04 (d, J=8.1 Hz, 1H); ESI-MS (m/z) 406.34 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08487121B2
Source dataset	uspto-grants-2013_07
ORD ID	ord-ca1ed5624ea0447bbed871dbcd618669
Source note	uspto-grants-2013_07