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

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	(2-Nitrophenyl)acetic acid	HCID 77337	—
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)-2-(2-nitrophenyl)acetamide	HCID 68794524	79.5%

Reaction Steps

This compound was prepared from Intermediate 2 (500 mg, 1.923 mmol) and 2-nitrophenylacetic acid (348 mg, 1.923 mmol) in presence of EDCI.HCl (191 mg, 1.789 mmol), HOBt (153 mg, 1.789 mmol) and triethylamine (802 μl, 2.289 mmol) in dichloromethane (10 ml) as described in Example 1 for 6 h to give 550 mg of the product as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.67-1.84 (m, 5H), 2.10-2.18 (m, 2H), 2.32-2.43 (m, 2H), 3.91 (s, 2H), 5.19-5.27 (m, 1H), 5.92-5.98 (m, 1H), 6.71 (d, J=9.3 Hz, 1H), 7.00-7.08 (m, 1H), 7.45-7.53 (m, 2H), 7.64 (d, J=7.5 Hz, 1H), 8.05 (d, J=8.9 Hz, 1H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08487121B2
Source dataset	uspto-grants-2013_07
ORD ID	ord-d89178d1a5244faf867d95b5792f3d21
Source note	uspto-grants-2013_07