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Methylamine → (Z)-4-(1-(4-hydroxyphenyl)-1-(4-(2-(methylamino)ethoxy) phenyl)but-1-en-2-yl)-1-methylpyridin-2(1H)-one

HRID 626190
Notes
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Reaction equation

HRID 626190 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=[C:12]([C:15]2[CH:20]=[CH:19][N:18]([CH3:21])[C:17](=[O:22])[CH:16]=2)[CH2:13][CH3:14])=[CH:7][CH:6]=1.[CH3:30][NH2:31]>CO>[OH:29][C:26]1[CH:27]=[CH:28][C:23](/[C:11](/[C:8]2[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][NH:31][CH3:30])=[CH:6][CH:7]=2)=[C:12](/[C:15]2[CH:20]=[CH:19][N:18]([CH3:21])[C:17](=[O:22])[CH:16]=2)\[CH2:13][CH3:14])=[CH:24][CH:25]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6329MethylamineHCID 1212666934-(1-(4-(2-chloroethoxy)phenyl)-1-(4-hydroxyphenyl)-but-1-en-2-yl)-1-methylpyridin-2(1H)-one

Product 1

HCID 71617487(Z)-4-(1-(4-hydroxyphenyl)-1-(4-(2-(methylamino)ethoxy) phenyl)but-1-en-2-yl)-1-methylpyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of 4-(1-(4-(2-chloroethoxy)phenyl)-1-(4-hydroxyphenyl)-but-1-en-2-yl)-1-methylpyridin-2(1H)-one (30 mg, 1.0 eq) in 10 mL MeOH was added 5 mL 30% CH3NH2 (aq), and the mixture was then heated at 85° C. for 36 h. Then the solvent was removed in vacuo, water was added to the residue and extracted with EtOAc. The extract was dried, concentrated, and purified by column chromatography to give the desired product (3 mg, Z-isomer), E-isomer (2 mg), and Z/E mixture (230 mg, 49% yield) as well. 1H NMR (400 MHz, CDCl3) δ 6.96-6.98 (m, 3H), 6.84 (d, J=8.8 Hz, 2H), 6.77 (d, J=8.4 Hz, 2H), 6.57 (d, J=8.8 Hz, 2H), 6.47 (d, J=2.0 Hz, 1H), 5.78 (dd, J=6.8 Hz, 2.0 Hz, 1H), 3.98 (t, J=5.2 Hz, 2H), 3.47 (s, 3H), 2.96 (t, J=5.2 Hz, 2H), 2.52 (s, 3H), 2.36-2.38 (m, 2H), 0.92 (t, J=7.2 Hz, 3H); m/z=405[M+1]+.

Workup

  1. customThen the solvent was removed in vacuo, water
  2. additionwas added to the residue
  3. extractionextracted with EtOAc
  4. customThe extract was dried
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-da29ee7b102849e1a7b6245b8051ca4f
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09309211B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes