2-(Ethylamino)ethanol → 2-(4-(2-(Ethyl(3,3,3-trifluoropropyl)amino)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol

Participants

Role	Name	HCID	Charge
Reactant	2-(Ethylamino)ethanol	HCID 8072	—
Reactant	1,1,1-Trifluoro-3-iodopropane	HCID 156165	—
Reactant	2-(4-iodophenyl)-4-methyl-6-((tetrahydro-2H-pyran-2-yl)oxy)-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)-2H-chromene	HCID 86682885	—
Product	2-(4-(2-(Ethyl(3,3,3-trifluoropropyl)amino)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol	HCID 89634474	—

Reaction Steps

The title compound was synthesized as described in general procedures F, I and J (z=1) using Intermediate 3 and 2-(ethylamino)ethanol in general procedure F, and 1,1,1-trifluoro-3-iodopropane in general procedure I. 1H NMR (400 MHz, DMSO-d6): δ 9.43 (s, 1H), 8.94 (s, 1H), 7.20 (d, 2H), 7.13 (t, 1H), 6.78 (d, 2H), 6.75-6.71 (m, 1H), 6.68 (d, 1H), 6.66-6.62 (m, 1H), 6.62-6.60 (m, 1H), 6.46 (s, 2H), 5.84 (s, 1H), 3.93 (t, 2H), 2.76 (t, 2H), 2.70 (t, 2H), 2.57-2.49 (m, 2H), 2.45-2.31 (m, 2H), 2.03 (s, 3H), 0.94 (t, 3H). LCMS: 514.1 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09193714B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-f0a9dd87869e46b5af60f5af041c946f
Source note	uspto-grants-2015_11