3-Hydroxy-5-methoxybenzaldehyde → 2-(3-Methoxy-5-{methyl-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethyl]-carbamoyl}-phenoxy)-2-methyl-propionic acid ethyl ester
Reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[C:5]([CH3:20])=[N:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1.[CH2:21]([O:23][C:24]([C:26]([CH3:40])([O:28][C:29]1[CH:30]=[C:31]([CH:35]=[C:36]([O:38][CH3:39])[CH:37]=1)[C:32]([OH:34])=O)[CH3:27])=[O:25])[CH3:22].OC1C=C(C=C(OC)C=1)C=O.C(CC(Br)(C)C([O-])=O)C.Cl([O-])=O.[Na+]>>[CH2:21]([O:23][C:24](=[O:25])[C:26]([O:28][C:29]1[CH:30]=[C:31]([C:32](=[O:34])[N:2]([CH3:1])[CH2:3][C:4]2[C:5]([CH3:20])=[N:6][C:7]([C:10]3[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:17])[F:18])=[CH:12][CH:11]=3)=[CH:8][CH:9]=2)[CH:35]=[C:36]([O:38][CH3:39])[CH:37]=1)([CH3:27])[CH3:40])[CH3:22]Participants
6
Reactant 5
Product 1
Procedure
A] In analogy to the procedures described in example 26B] and 26C], methyl-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethyl]-amine (example 123D]) was reacted with 3-(1-ethoxycarbonyl-1-methyl-ethoxy)-5-methoxy-benzoic acid (prepared from 3-hydroxy-5-methoxy-benzaldehyde [Journal of Organic Chemistry (1985), 50(13), 2236–40], by reaction with ethyl-bromoisobutyrate followed by oxidation with sodium chlorite in analogy to the procedures described in examples 52A] and 59A]) to give 2-(3-methoxy-5-{methyl-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethyl]-carbamoyl}-phenoxy)-2-methyl-propionic acid ethyl ester, which was subsequently saponified to yield the title compound as colorless solid.
Sources & evidence
- ORD record
- ord-a7721dfbb37b46f6b91c18a2f120eb0d
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115611B2
Reaction notes
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