Methyl 5-methoxy-3-oxopentanoate → 2-[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:17])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH2:16])=[CH:11][CH:10]=1)([CH3:7])[CH3:6])[CH3:2].[CH3:18][O:19][CH2:20][CH2:21][C:22]1[C:27]([C:28](O)=[O:29])=[CH:26][N:25]=[C:24]([C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=2)[N:23]=1.COC(=O)CC(=O)CCOC>>[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][NH:16][C:28]([C:27]2[C:22]([CH2:21][CH2:20][O:19][CH3:18])=[N:23][C:24]([C:31]3[CH:32]=[CH:33][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:35][CH:36]=3)=[N:25][CH:26]=2)=[O:29])=[CH:13][CH:14]=1)([CH3:7])[CH3:6])[CH3:2]Participants
4
Reactant 3
Product 1
Procedure
In analogy to the procedures described in example 26B] and 26C], 2-(4-aminomethyl-phenoxy)-2-methyl-propionic acid ethyl ester [PCT Int. Appl. (2002), WO 2002/096895A1] 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-[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 solid.
Sources & evidence
- ORD record
- ord-c43ca6837d8e4dc9ace40850016a3b48
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115611B2
Reaction notes
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