Reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[C:11]([O:19][CH3:20])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:21][C:22]1[C:23]([CH3:29])=[N:24][N:25]([CH2:27][CH3:28])[CH:26]=1>>[CH2:27]([N:25]1[CH:26]=[C:22]([NH:21][C:16](=[O:18])[CH2:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][C:11]=2[O:19][CH3:20])[C:23]([CH3:29])=[N:24]1)[CH3:28]Participants
Procedure
Using an analogous procedure to that described in the portion of Example 17 that is concerned with the preparation of starting materials, 2-(4-benzyloxy-2-methoxyphenyl)acetic acid was reacted with 4-amino-1-ethyl-3-methylpyrazole to give N-(1-ethyl-3-methylpyrazol-4-yl)-2-(4-benzyloxy-2-methoxyphenyl)acetamide; 1H NMR: (DMSOd6) 1.29 (t, 3H), 2.1 (s, 3H), 3.5 (s, 2H), 3.75 (s, 3H), 3.96 (q, 2H), 5.09 (s, 2H), 6.54 (m, 1H), 6.63 (d, 1H), 7.06 (d, 1H), 7.33 (m, 1H), 7.39 (m, 2H), 7.45 (m, 2H), 7.8 (s, 1H), 9.29 (s, 1H); Mass Spectrum: M+H+ 380; which material was hydrogenated to give N-(1-ethyl-3-methylpyrazol-4-yl)-2-(4-hydroxy-2-methoxyphenyl)acetamide; 1H NMR: (DMSOd6) 1.28 (t, 3H), 2.1 (s, 3H), 3.45 (s, 2H), 3.7 (s, 3H), 3.96 (q, 2H), 6.28 (m, 1H), 6.37 (d, 1H), 6.93 (d, 1H), 7.8 (s, 1H), 9.22 (br s, 1H), 9.29 (br s, 1H); Mass Spectrum: M+H+ 290.
Sources & evidence
- ORD record
- ord-0f8e115168c9433fb464c8075cd01fc8
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07973164B2
Linked notes
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