4-Fluorophenol → HCID 59262193, compound

HRID 534751Notes

Reaction equation

HRID 534751 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]([CH3:33])[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)=[C:13]([F:32])[CH:12]=2)=[O:9])=[CH:4][CH:3]=1.[F:34][C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=1>>[F:32][C:13]1[CH:12]=[C:11]([N:10]([C:8]([C:5]2[CH:6]=[N:7][C:2]([O:41][C:38]3[CH:39]=[CH:40][C:35]([F:34])=[CH:36][CH:37]=3)=[CH:3][CH:4]=2)=[O:9])[CH3:33])[CH:16]=[CH:15][C:14]=1[CH2:17][N:18]1[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]1

Participants

3

Reactant 2

HCID 97324-FluorophenolHCID 59262243HCID 59262243, compound

Product 1

HCID 59262193HCID 59262193, compound

Procedure

The title compound was prepared from 1,1-dimethylethyl (2S)-4-({4-[[(6-chloro-3-pyridinyl)carbonyl](methyl)amino]-2-fluorophenyl}methyl)-2-methyl-1-piperazinecarboxylate (D70) and 4-fluorophenol using a method similar to that described for D55 in Description 55 although the reaction temp./time was 130° C. for 8 h and purification was carried out by column chromatography. δH (CDCl3, 400 MHz) 8.07 (1H, dd), 7.70 (1H, dd), 7.33 (1H, t), 7.05 (4H, m), 6.78 (3H, m), 4.19 (1H, br.s), 3.81 (1H, d), 3.47 (5H, m), 3.07 (1H, td), 2.71 (1H, d), 2.53 (1H, d), 2.18 (1H, dd), 2.04 (1H, m), 1.46 (9H, s), 1.20 (3H, d).

Workup

  1. custompurification

Sources & evidence

ORD record
ord-81fbaf82f41b493597d0c71aa228ada1
Source dataset
uspto-grants-2014_10
Patent number
US08853218B2

Reaction notes

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