2-Chloro-4-hydroxybenzaldehyde → 2-[3-Chloro-4-({[4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carbonyl]-amino}-methyl)-phenoxy]-2-methyl-propionic acid ethyl ester
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.[F:38][C:39]([F:60])([F:59])[C:40]1[C:45]([C:46](O)=[O:47])=[CH:44][N:43]=[C:42]([C:49]2[CH:54]=[CH:53][C:52]([C:55]([F:58])([F:57])[F:56])=[CH:51][CH:50]=2)[N:41]=1.C(OC(C1C(C(F)(F)F)=NC(C2C=CC(C(F)(F)F)=CC=2)=NC=1)=O)C>>[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:46]([C:45]2[C:40]([C:39]([F:60])([F:38])[F:59])=[N:41][C:42]([C:49]3[CH:50]=[CH:51][C:52]([C:55]([F:57])([F:58])[F:56])=[CH:53][CH:54]=3)=[N:43][CH:44]=2)=[O:47])=[C:11]([Cl:17])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2]Participants
Reactant 5
Product 1
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 4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid (prepared by saponification from 4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid ethyl ester (example 107B]) in analogy to example 53B]) to give 2-[3-chloro-4-({[4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carbonyl]-amino}-methyl)-phenoxy]-2-methyl-propionic acid ethyl ester, which was subsequently saponified to yield the title compound as amorphous light yellow solid.
Sources & evidence
- ORD record
- ord-a4617bc5400d44fcb06cbea954e86628
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115611B2
Reaction notes
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