2-Chloro-4-hydroxybenzaldehyde → 2-[3-Chloro-4-({[4-cyclopropyl-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.[CH:38]1([C:41]2[C:46]([C:47](O)=[O:48])=[CH:45][N:44]=[C:43]([C:50]3[CH:55]=[CH:54][C:53]([C:56]([F:59])([F:58])[F:57])=[CH:52][CH:51]=3)[N:42]=2)[CH2:40][CH2:39]1>>[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:47]([C:46]2[C:41]([CH:38]3[CH2:40][CH2:39]3)=[N:42][C:43]([C:50]3[CH:51]=[CH:52][C:53]([C:56]([F:58])([F:59])[F:57])=[CH:54][CH:55]=3)=[N:44][CH:45]=2)=[O:48])=[C:11]([Cl:17])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2]Participants
5
Reactant 4
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-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid (example 53B]) to give 2-[3-chloro-4-({[4-cyclopropyl-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 colorless solid.
Sources & evidence
- ORD record
- ord-4cdf8dded70844bf82059c1264dc06f4
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115611B2
Reaction notes
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