Methyl-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-amine → 2-Methyl-2-[4-({methyl-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-carbamoyl}-methyl)-phenoxy]-propionic acid tert-butyl ester
Reaction equation
[CH3:1][NH:2][C:3]1[C:4]([CH3:19])=[N:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1.C(OC(=O)NC1C(C)=NC(C2C=CC(C(F)(F)F)=CC=2)=CC=1)(C)(C)C.[C:45]([O:49][C:50](=[O:65])[C:51]([O:54][C:55]1[CH:60]=[CH:59][C:58]([CH2:61][C:62]([OH:64])=O)=[CH:57][CH:56]=1)([CH3:53])[CH3:52])([CH3:48])([CH3:47])[CH3:46]>>[C:45]([O:49][C:50](=[O:65])[C:51]([CH3:52])([O:54][C:55]1[CH:56]=[CH:57][C:58]([CH2:61][C:62](=[O:64])[N:2]([CH3:1])[C:3]2[C:4]([CH3:19])=[N:5][C:6]([C:9]3[CH:10]=[CH:11][C:12]([C:15]([F:18])([F:16])[F:17])=[CH:13][CH:14]=3)=[CH:7][CH:8]=2)=[CH:59][CH:60]=1)[CH3:53])([CH3:46])([CH3:47])[CH3:48]Participants
4
Reactant 3
Product 1
Procedure
In analogy to the procedures described in example 26B] and 124C], methyl-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-amine (prepared from [2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-carbamic acid tert-butyl ester (example 125B] by N-methylation followed by Boc-cleavage in analogy to the procedures described in examples 5E] and 5F]) was reacted with 2-(4-carboxymethyl-phenoxy)-2-methyl-propionic acid tert-butyl ester (example 124A]) to give 2-methyl-2-[4-({methyl-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-carbamoyl}-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-31fb934902044d76898ed2124622393d
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115611B2
Reaction notes
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