2-Chloro-4-hydroxybenzaldehyde → 2-[3-Chloro-4-({[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine-3-carbonyl]-amino}-methyl)-phenoxy]-2-methyl-propionic acid ethyl ester

HRID 1242483Notes

Reaction equation

HRID 1242483 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH2:16])=[C:11]([Cl:17])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2].ClC1C=C(O)C=CC=1C=O.C(CC(Br)(C)C([O-])=O)C.[CH3:38][C:39]1[N:47]=[C:46]([C:48]2[CH:53]=[CH:52][C:51]([C:54]([F:57])([F:56])[F:55])=[CH:50][CH:49]=2)[CH:45]=[CH:44][C:40]=1[C:41](O)=[O:42].COC(=O)C1C=CC(C2C=CC(C(F)(F)F)=CC=2)=NC=1C>>[CH2:1]([O:3][C:4](=[O:18])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:41]([C:40]2[C:39]([CH3:38])=[N:47][C:46]([C:48]3[CH:53]=[CH:52][C:51]([C:54]([F:57])([F:55])[F:56])=[CH:50][CH:49]=3)=[CH:45][CH:44]=2)=[O:42])=[C:11]([Cl:17])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2]

Participants

6

Reactant 5

HCID 1853632-Chloro-4-hydroxybenzaldehydeHCID 219358852-Methyl-6-(4-trifluoromethyl-phenyl)-nicotinic acidHCID 22490247Ethyl-bromoisobutyrateHCID 670722692-Methyl-6-(4-trifluoromethyl-phenyl)-nicotinic Acid Methyl EsterHCID 670725432-(4-Aminomethyl-3-chloro-phenoxy)-2-methyl-propionic acid ethyl ester

Product 1

HCID 695254802-[3-Chloro-4-({[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine-3-carbonyl]-amino}-methyl)-phenoxy]-2-methyl-propionic acid ethyl ester

Procedure

In analogy to the procedures described in example 26B] and 26C], 2-(4-aminomethyl-3-chloro-phenoxy)-2-methyl-propionic acid ethyl ester (prepared from 2-chloro-4-hydroxy-benzaldehyde by reaction with ethyl-bromoisobutyrate as described in example 52A] followed by oxim formation and reduction as described in examples 97A] and 97B]) was reacted with 2-methyl-6-(4-trifluoromethyl-phenyl)-nicotinic acid (prepared from 2-methyl-6-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester (example 1L]) in analogy to the procedure described in example 53B]) to give 2-[3-chloro-4-({[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine-3-carbonyl]-amino}-methyl)-phenoxy]-2-methyl-propionic acid ethyl ester, which was subsequently saponified to yield the title compound as light yellow foam.

Sources & evidence

ORD record
ord-2208a69f4ea042999c85c5fd691ff292
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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