2-Chloro-4-hydroxybenzaldehyde → 2-[3-Chloro-4-({[4-(2-methoxy-ethyl)-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.[CH3:38][O:39][CH2:40][CH2:41][C:42]1[C:47]([C:48](O)=[O:49])=[CH:46][N:45]=[C:44]([C:51]2[CH:56]=[CH:55][C:54]([C:57]([F:60])([F:59])[F:58])=[CH:53][CH:52]=2)[N:43]=1.COC(=O)CC(=O)CCOC>>[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:48]([C:47]2[C:42]([CH2:41][CH2:40][O:39][CH3:38])=[N:43][C:44]([C:51]3[CH:52]=[CH:53][C:54]([C:57]([F:60])([F:59])[F:58])=[CH:55][CH:56]=3)=[N:45][CH:46]=2)=[O:49])=[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-(2-methoxy-ethyl)-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid (prepared from 5-methoxy-3-oxo-pentanoic acid methyl ester, in analogy to the procedures described in examples 27C] and 27D] followed by saponification in analogy to the procedure described in example 53B]) to give 2-[3-chloro-4-({[4-(2-methoxy-ethyl)-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 light yellow oil.
Sources & evidence
- ORD record
- ord-3a5580c47b294b50b81f6afcc20a3c32
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115611B2
Reaction notes
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