Methylamine → HCID 71615975, compound

HRID 626246Notes

Reaction equation

HRID 626246 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8](/[C:11](/[C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[C:12](/[C:15]2[CH:24]=[CH:23][C:18]3[N:19]([CH3:22])[CH:20]=[N:21][C:17]=3[CH:16]=2)\[CH2:13][CH3:14])=[CH:7][CH:6]=1.[CH3:32][NH2:33]>CO>[CH3:22][N:19]1[C:18]2[CH:23]=[CH:24][C:15](/[C:12](/[CH2:13][CH3:14])=[C:11](\[C:25]3[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=3)/[C:8]3[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][NH:33][CH3:32])=[CH:6][CH:7]=3)=[CH:16][C:17]=2[N:21]=[CH:20]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 121266689HCID 121266689, compound

Product 1

HCID 71615975HCID 71615975, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to the same procedure as example 1, step E described, (E)-4-(1-(4-(2-chloroethoxy)phenyl)-2-(1-methyl-1H-benzo[d]imidazol-5-yl)but-1-enyl)phenol (made by example 8, step F) was reacted with MeNH2 (30% wt in water) in MeOH under reflux to give the desired (E)-product. 1H NMR (400 MHz, CDCl3) δ 7.78 (s, 1H), 7.63 (s, 1H), 7.18 (d, J=8.8 Hz, 2H), 7.13 (d, J=8.4 Hz, 1H), 7.01 (dd, J=8.4 Hz, 1.2 Hz, 1H), 6.88 (d, J=8.8 Hz, 2H), 6.72 (d, J=8.4 Hz, 2H), 6.40 (d, J=8.4 Hz, 2H), 4.10 (t, J=5.2 Hz, 2H), 3.77 (s, 3H), 2.99 (t, J=5.2 Hz, 2H), 2.50-2.55 (m, 5H), 0.91 (t, J=7.2 Hz, 3H); m/z=428[M+1]+.

Workup

  1. temperatureunder reflux
  2. customto give the desired (E)-product

Sources & evidence

ORD record
ord-7454bb1c480f46bf9996c98352263303
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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