2-Methyl-6-(4-(trifluoromethyl)phenyl)pyridin-3-amine → 2-Methyl-2-(4-{[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylcarbamoyl]-methyl}-phenoxy)-propionic acid tert-butyl ester

HRID 1242480Notes

Reaction equation

HRID 1242480 reaction equation
[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[N:3]=1.[C:19]([O:23][C:24](=[O:39])[C:25]([O:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][C:36](O)=[O:37])=[CH:31][CH:30]=1)([CH3:27])[CH3:26])([CH3:22])([CH3:21])[CH3:20]>>[C:19]([O:23][C:24](=[O:39])[C:25]([CH3:26])([O:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][C:36](=[O:37])[NH:8][C:7]2[C:2]([CH3:1])=[N:3][C:4]([C:9]3[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:18])[F:17])=[CH:11][CH:10]=3)=[CH:5][CH:6]=2)=[CH:31][CH:30]=1)[CH3:27])([CH3:21])([CH3:20])[CH3:22]

Participants

3

Reactant 2

HCID 219358322-Methyl-6-(4-(trifluoromethyl)phenyl)pyridin-3-amineHCID 670720574-Carboxymethyl-phenoxy-2-methyl-propionic acid tert-butyl ester

Product 1

HCID 670722212-Methyl-2-(4-{[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylcarbamoyl]-methyl}-phenoxy)-propionic acid tert-butyl ester

Procedure

A] In analogy to the procedures described in example 26B] and 124C], 2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylamine (example 125C]) was reacted with 2-(4-carboxymethyl-phenoxy)-2-methyl-propionic acid tert-butyl ester (example 124A]) to give 2-methyl-2-(4-{[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylcarbamoyl]-methyl}-phenoxy)-propionic acid tert-butyl ester, which was subsequently cleaved with trifluoroacetic acid to yield the title compound as colorless solid.

Sources & evidence

ORD record
ord-63f52ad6ac3840d6b1735199fed86a0f
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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