Triethylamine → HCID 68792411, compound

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	HCID 19617788	HCID 19617788	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 68792411	HCID 68792411	66.7%

Reaction Steps

This compound was prepared from Intermediate 2 (500 mg, 1.938 mmol) and (2E)-3-[2-(benzyloxy)-3-methoxyphenyl]acrylic acid (575 mg, 2.023 mmol) in presence of EDCI.HCl (555 mg, 2.897 mmol), HOBt (443 mg, 2.897 mmol) and triethylamine (806 μl, 5.791 mmol) in dichloromethane (15 ml) as described in Example 1 to give 633 mg of the product as a white solid; 1H NMR (300 MHz, CDCl3) δ 1.70-1.84 (m, 3H), 2.11-2.22 (m, 3H), 2.35-2.47 (m, 2H), 3.89 (s, 3H), 5.02 (q, J=11.4 Hz, 2H), 5.34 (q, J=9.9 Hz, 1H), 5.44 (d, J=8.4 Hz, 1H), 6.59 (d, J=15.6 Hz, 1H), 6.75 (d, J=8.4 Hz, 1H), 6.92-6.96 (m, 1H), 7.04-7.10 (m, 4H), 7.19-7.29 (m, 3H), 7.41 (d, J=6.6 Hz, 2H), 7.69 (d, J=16.2 Hz, 1H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08487121B2
Source dataset	uspto-grants-2013_07
ORD ID	ord-dc2eed3d38714d09982f8562f3dc5f98
Source note	uspto-grants-2013_07