Ethyl 3-oxoheptanoate → 2-[3-({2-[4-Butyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-acetyl}-methyl-amino)-phenoxy]-2-methyl-propionic acid ethyl ester

HRID 1242383Notes

Reaction equation

HRID 1242383 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]([CH3:16])([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][CH3:15])[CH:9]=1)[CH3:6])[CH3:2].[CH2:18]([C:22]1[C:27]([CH2:28][C:29](O)=[O:30])=[CH:26][N:25]=[C:24]([C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=2)[N:23]=1)[CH2:19][CH2:20][CH3:21].C(OC(=O)CC(=O)CCCC)C>>[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]([C:29](=[O:30])[CH2:28][C:27]2[C:22]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:23][C:24]([C:32]3[CH:33]=[CH:34][C:35]([C:38]([F:40])([F:41])[F:39])=[CH:36][CH:37]=3)=[N:25][CH:26]=2)[CH3:15])[CH:9]=1)([CH3:16])[CH3:6])[CH3:2]

Participants

4

Reactant 3

HCID 559036Ethyl 3-oxoheptanoateHCID 21935713[4-Butyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-acetic acidHCID 670721182-Methyl-2-(3-methylamino-phenoxy)-propionic acid ethyl ester

Product 1

HCID 670723972-[3-({2-[4-Butyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-acetyl}-methyl-amino)-phenoxy]-2-methyl-propionic acid ethyl ester

Procedure

In analogy to the procedures described in example 26B] and 26C], 2-methyl-2-(3-methylamino-phenoxy)-propionic acid ethyl ester (example 26 A]) was reacted with [4-butyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-acetic acid (prepared starting from 3-oxo-heptanoic acid ethyl ester in analogy to the sequences described in examples 27C] to 27F] and examples 26D] and 26E]) to give 2-[3-({2-[4-butyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-acetyl}-methyl-amino)-phenoxy]-2-methyl-propionic acid ethyl ester, which was subsequently saponified to yield the title compound as light yellow amorphous solid.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-ee3e5fda1f014b38aa53672edc108e89
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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