3-Cyanophenol → 1,1-Dimethylethyl (2S)-4-({4-[({5-[(3-cyanophenyl)oxy]-2-pyridinyl}carbonyl)(methyl)amino]phenyl}methyl)-2-methyl-1-piperazinecarboxylate

HRID 534757Notes

Reaction equation

HRID 534757 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:10]([CH3:32])[C:11]2[CH:16]=[CH:15][C:14]([CH2:17][N:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@@H:20]([CH3:31])[CH2:19]3)=[CH:13][CH:12]=2)=[O:9])=[N:6][CH:7]=1.[C:33]([C:35]1[CH:36]=[C:37]([OH:41])[CH:38]=[CH:39][CH:40]=1)#[N:34]>>[C:33]([C:35]1[CH:36]=[C:37]([O:41][C:2]2[CH:3]=[CH:4][C:5]([C:8]([N:10]([CH3:32])[C:11]3[CH:16]=[CH:15][C:14]([CH2:17][N:18]4[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@@H:20]([CH3:31])[CH2:19]4)=[CH:13][CH:12]=3)=[O:9])=[N:6][CH:7]=2)[CH:38]=[CH:39][CH:40]=1)#[N:34]

Participants

3

Reactant 2

HCID 133943-CyanophenolHCID 592622381,1-Dimethylethyl (2S)-4-({4-[[(5-bromo-2-pyridinyl)carbonyl](methyl)amino]phenyl}methyl)-2-methyl-1-piperazinecarboxylate

Product 1

HCID 592621951,1-Dimethylethyl (2S)-4-({4-[({5-[(3-cyanophenyl)oxy]-2-pyridinyl}carbonyl)(methyl)amino]phenyl}methyl)-2-methyl-1-piperazinecarboxylate

Procedure

The title compound was prepared from 1,1-dimethylethyl (2S)-4-({4-[[(5-bromo-2-pyridinyl)carbonyl](methyl)amino]phenyl}methyl)-2-methyl-1-piperazinecarboxylate (D72) and 3-cyanophenol using a method similar to that described for D73 in Description 73 although the reaction was worked up after the first night of heating. MS (ES): MH+ 542.3.

Workup

  1. temperatureof heating

Sources & evidence

ORD record
ord-52d1d768e9504408931fe425fdf20b56
Source dataset
uspto-grants-2014_10
Patent number
US08853218B2

Reaction notes

Loading…