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

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	2-Pyridineacetic acid	HCID 85318	—
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-pyridin-2-ylacetamide	HCID 44132277	—

Reaction Steps

The title compound was prepared from Intermediate 2 (200 mg, 0.898 mmol) and 2-pyridylacetic acid (234 mg, 1.348 mmol) in presence of EDCI.HCl (258 mg, 1.348 mmol), HOBt (206 mg, 1.348 mmol) and triethylamine (375 μl, 2.696 mmol) in dichloromethane (10 ml) as described in Example 1 to give 151 mg of the product as a white solid; IR (KBr) 3272, 2936, 1644, 1477, 1265, 812 cm−1; 1H NMR (300 MHz, DMSO-d6) δ 1.65-1.88 (m, 3H), 2.02-2.20 (m, 3H), 2.25-2.35 (m, 2H), 3.71 (q, J=12.0 Hz, 2H), 5.00-5.15 (m, 1H), 6.73 (t, J=7.8 Hz, 1H), 6.76 (d, J=8.4 Hz, 1H), 7.10-7.20 (m, 2H), 7.22-7.30 (m, 1H), 7.70-7.80 (m, 1H), 8.49 (s, 1H), 8.62 (d, J=8.4 Hz, 1H); ESI-MS (m/z) 343.21 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08487121B2
Source dataset	uspto-grants-2013_07
ORD ID	ord-6cdbf3dfb03d4735b1565795d6602ff2
Source note	uspto-grants-2013_07