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

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
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	—
Reactant	[2-(Cyclopentyloxy)-3-methoxyphenyl]acetic acid	HCID 68628470	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-(6-Chloro-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-4-yl)-2-(2-(cyclopentyloxy)-3-methoxyphenyl)acetamide	HCID 44132274	—

Reaction Steps

The title compound was prepared from Intermediate 2 (200 mg, 0.763 mmol) in dichloromethane (10 ml) and [2-(cyclopentyloxy)-3-methoxyphenyl]acetic acid (283 mg, 1.153 mmol) in presence of EDCI.HCl (221 mg, 1.153 mmol), HOBt (178 mg, 1.153 mmol) and triethylamine (321 μl, 2.307 mmol) as described in Example 1 to give 236 mg of the product as a white solid; IR (KBr) 3311, 2963, 1653, 1529, 1476, 1266, 813 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.58-1.64 (m, 6H), 1.70-1.80 (m, 6H), 1.97-2.04 (m, 1H), 2.13 (t, J=7.8 Hz, 2H), 2.26-2.33 (m, 2H), 3.58 (q, J=14.4 Hz, 2H), 3.81 (s, 3H), 4.99 (br s, 1H), 5.09-5.17 (m, 1H), 6.31 (d, J=8.1 Hz, 1H), 6.66 (t, J=8.4 Hz, 1H), 6.81-7.02 (m, 4H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08487121B2
Source dataset	uspto-grants-2013_07
ORD ID	ord-0f73b48417a140179b2a199f47779261
Source note	uspto-grants-2013_07