3-Cyanophenol → 1,1-Dimethylethyl (2S)-4-({4-[({6-[(3-cyanophenyl)oxy]-3-pyridinyl}carbonyl)(methyl)amino]phenyl}methyl)-2-methyl-1-piperazinecarboxylate

HRID 534738Notes

Reaction equation

HRID 534738 reaction equation
Cl[C:2]1[N:7]=[CH:6][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])=[CH:4][CH:3]=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[N:7]=[CH:6][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])=[CH:4][CH:3]=2)[CH:38]=[CH:39][CH:40]=1)#[N:34]

Participants

3

Reactant 2

HCID 133943-CyanophenolHCID 592622291,1-Dimethylethyl (2S)-4-({4-[[(6-chloro-3-pyridinyl)carbonyl](methyl)amino]phenyl}methyl)-2-methyl-1-piperazinecarboxylate

Product 1

HCID 592621861,1-Dimethylethyl (2S)-4-({4-[({6-[(3-cyanophenyl)oxy]-3-pyridinyl}carbonyl)(methyl)amino]phenyl}methyl)-2-methyl-1-piperazinecarboxylate

Procedure

The title compound was prepared from 1,1-dimethylethyl (2S)-4-({4-[[(6-chloro-3-pyridinyl)carbonyl](methyl)amino]phenyl}methyl)-2-methyl-1-piperazinecarboxylate (D54) and 3-cyanophenol in a similar manner to that described for D55 in Description 55 although the reaction temp./time was 130° C. for 24 h and purification was carried out by column chromatography. This gave the title compound as a colourless oil (0.184 g). MS (ES): MH+ 542.3.

Workup

  1. custompurification

Sources & evidence

ORD record
ord-6b2608da75f440b4ab8c961db1993a7c
Source dataset
uspto-grants-2014_10
Patent number
US08853218B2

Reaction notes

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