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

HRID 534756Notes

Reaction equation

HRID 534756 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.[F:33][C:34]1[CH:35]=[C:36]([OH:40])[CH:37]=[CH:38][CH:39]=1.CC(CCCC(CCCC(CCCC(CCC(O)=O)C)C)C)C>Cl[Cu]>[F:33][C:34]1[CH:35]=[C:36]([O:40][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:37]=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 97433-FluorophenolHCID 30806684,8,12,16-Tetramethylheptadecanoic acidHCID 592622381,1-Dimethylethyl (2S)-4-({4-[[(5-bromo-2-pyridinyl)carbonyl](methyl)amino]phenyl}methyl)-2-methyl-1-piperazinecarboxylate

Product 1

HCID 592621841,1-Dimethylethyl (2S)-4-({4-[({5-[(3-fluorophenyl)oxy]-2-pyridinyl}carbonyl)(methyl)amino]phenyl}methyl)-2-methyl-1-piperazinecarboxylate

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

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-fluorophenol using a method similar to that described for D73 in Description 73 although 1 eq. CuCl and 0.25 eq. THMD were used. MS (ES): MH+ 535.3.

Sources & evidence

ORD record
ord-4236b5af72f54bf18c063032af5a22c5
Source dataset
uspto-grants-2014_10
Patent number
US08853218B2

Reaction notes

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