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

HRID 717513Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24]C4CCCCO4)[CH:19]=3)=[C:16]([CH3:31])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:32]C4CCCCO4)[CH:14]=3)[O:9]2)=[CH:4][CH:3]=1.[CH2:39]([NH:41][CH2:42][CH2:43][OH:44])[CH3:40].[F:45][CH2:46][CH2:47][CH2:48]I>>[CH2:39]([N:41]([CH2:48][CH2:47][CH2:46][F:45])[CH2:42][CH2:43][O:44][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=3)=[C:16]([CH3:31])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([OH:32])[CH:14]=3)[O:9]2)=[CH:4][CH:3]=1)[CH3:40]

Participants

Reactant 3

HCID 80722-(Ethylamino)ethanol

HCID 128991281-Iodo-3-fluoropropane

HCID 866828852-(4-iodophenyl)-4-methyl-6-((tetrahydro-2H-pyran-2-yl)oxy)-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)-2H-chromene

Product 1

HCID 896344732-(4-(2-(Ethyl(3-fluoropropyl)amino)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol

Procedure

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-fluoro-3-iodopropane in general procedure I. 1H NMR (400 MHz, DMSO-d6): δ 9.43 (s, 1H), 8.94 (s, 1H), 7.19 (d, 2H), 7.13 (t, 1H), 6.78 (d, 2H), 6.76-6.72 (m, 1H), 6.68 (d, 1H), 6.67-6.62 (m, 1H), 6.62-6.60 (m, 1H), 6.48 (s, 2H), 5.84 (s, 1H), 4.50 (t, 1H), 4.39 (t, 1H), 3.91 (t, 2H), 2.72 (t, 2H), 2.58-2.45 (m, 4H), 2.03 (s, 3H), 1.80-1.71 (m, 1H), 1.71-1.65 (m, 1H), 0.93 (t, 3H). LCMS: 478.1 (M+H)+.

Sources & evidence

ORD record: ord-99ac52240aad45bf856f11350ecd8800
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193714B2

Reaction notes

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