Methylamine → 4-(2-(Benzo[d]oxazol-5-yl)-1-(4-(2-(methylamino)ethoxy)phenyl)but-1-enyl)phenol

HRID 626221Notes

Reaction equation

HRID 626221 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([CH2:29][CH3:30])=[C:11]([C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20]Cl)=[CH:14][CH:13]=3)=[CH:9][C:4]=2[N:3]=[CH:2]1.[CH3:31][NH2:32]>CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([CH2:29][CH3:30])=[C:11]([C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][NH:32][CH3:31])=[CH:14][CH:13]=3)=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 1239169244-(2-(Benzo[d]oxazol-5-yl)-1-(4-(2-chloroethoxy)phenyl)but-1-enyl)phenol

Product 1

HCID 781350054-(2-(Benzo[d]oxazol-5-yl)-1-(4-(2-(methylamino)ethoxy)phenyl)but-1-enyl)phenolYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to the same procedure as example 1, step E described, 4-(2-(benzo[d]oxazol-5-yl)-1-(4-(2-chloroethoxy)phenyl)but-1-enyl)phenol (0.1 g, 1.0 eq) was reacted with MeNH2 (30% wt in water, 10 mL) in MeOH (20 mL) under reflux to give 20 mg desired product (25%, Z/E=1/1). 1H NMR (400 MHz, CDCl3) δ 7.08 (d, J=8.4 Hz, 2H), 7.01 (d, J=8.8 Hz, 2H), 6.82 (d, J=8.4 Hz, 2H), 6.68-6.80 (m, 6H), 6.58-6.64 (m, 4H), 6.49-6.55 (m, 4H). 6.46 (d, J=8.8 Hz, 2H), 5.89 (s, 2H), 4.09 (t, J=5.6 Hz, 2H), 3.97 (t, J=5.2 Hz, 2H), 3.00 (t, J=5.2 Hz, 2H), 2.92 (t, J=5.6 Hz, 2H), 2.54 (s, 3H), 2.50 (s, 3H), 2.39-2.49 (m, 4H), 0.80-1.00 (m, 6H).

Workup

  1. temperatureunder reflux

Sources & evidence

ORD record
ord-75cb5526d8d34aa68a7322b47492cbb2
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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