Methylamine → 6-(1-(4-Hydroxyphenyl)-1-(4-(2-(methylamino)ethoxy)phenyl)-but-1-en-2-yl)pyridin-3-ol

HRID 626200Notes

Reaction equation

HRID 626200 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)=[C:12]([C:15]2[N:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH2:13][CH3:14])=[CH:7][CH:6]=1.[CH3:29][NH2:30]>CO>[OH:28][C:25]1[CH:26]=[CH:27][C:22]([C:11]([C:8]2[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][NH:30][CH3:29])=[CH:6][CH:7]=2)=[C:12]([C:15]2[N:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH2:13][CH3:14])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 1371468096-(1-(4-(2-Chloroethoxy)phenyl)-1-(4-hydroxyphenyl)but-en-2-yl)pyridin-3-ol

Product 1

HCID 1371617406-(1-(4-Hydroxyphenyl)-1-(4-(2-(methylamino)ethoxy)phenyl)-but-1-en-2-yl)pyridin-3-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following the same procedure as described in example 11, step D, 6-(1-(4-(2-chloroethoxy)phenyl)-1-(4-hydroxyphenyl)but-1-en-2-yl)pyridin-3-ol (0.22 g, 1.0 eq) was reacted with MeNH2 (30% wt in water, 10 mL) in MeOH (20 mL) under reflux to give the desired product (Z/E=1/1). 1H NMR (400 MHz, DMSO-d6) δ 9.31 (brs, 1H), 8.09 (d, J=2.4 Hz, 1H), 7.08 (d, J=8.0 Hz, 1H), 6.92-6.97 (m, 2H), 6.81 (d, J=8.8 Hz, 1H), 6.75 (d, J=8.4 Hz, 1H), 6.55-6.69 (m, 4H), 6.45 (d, J=8.4 Hz, 1H), 4.06 (t, J=5.2 Hz, 1H), 3.93 (t, J=5.2 Hz, 1H), 2.93 (t, J=5.6 Hz, 1H), 2.85 (t, J=5.6 Hz, 1H), 2.46-2.50 (m, 2H), 2.40 (s, 1.5H), 2.35 (s, 1.5H), 0.83 (t, J=7.2 Hz, 3H); m/z=391[M+1]+.

Workup

  1. temperatureunder reflux

Sources & evidence

ORD record
ord-2ce5438d56834cfc8931d25c5d2b5029
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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