1H-Indole-3-propanoic acid → HCID 44134163, compound

Participants

Role	Name	HCID	Charge
Reactant	1H-Indole-3-propanoic acid	HCID 3744	—
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	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 44134163	HCID 44134163	—

Reaction Steps

The title compound was prepared from Intermediate 2 (200 mg, 0.894 mmol) and 3-(1H-indol-3-yl)propanoic acid (187 mg, 0.988 mmol) in presence of EDCI.HCl (258 mg, 1.345 mmol), HOBt (206 mg, 1.345 mmol) and triethylamine (375 μl, 2.684 mmol) in dichloromethane (10 ml) as described in Example 1 to give 121 mg of the product as a white solid; IR (KBr) 3395, 2926, 1642, 1474, 1234, 748 cm−1; 1H NMR (300 MHz, CDCl3) δ 1.78-1.96 (m, 2H), 2.09-2.26 (m, 6H), 2.63 (t, J=6.3 Hz, 2H), 3.17-3.21 (m, 2H), 5.15 (q, J=9.6 Hz, 1H), 5.34 (d, J=8.4 Hz, 1H), 6.65 (d, J=8.7 Hz, 1H), 6.77 (s, 1H), 6.99-7.14 (m, 4H), 7.35 (d, J=7.8 Hz, 1H), 7.59 (d, J=7.8 Hz, 1H), 8.05 (s, 1H); ESI-MS (m/z) 395.63 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08487121B2
Source dataset	uspto-grants-2013_07
ORD ID	ord-58338ac07ab348599856c088870bb74a
Source note	uspto-grants-2013_07