4-(2-Methylpiperidin-1-YL)-3-(trifluoromethyl)benzoic acid → N-methyl-N-(3-{5-[4-(2-methylpiperidin-1-yl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}benzyl)glycine
Reaction equation
[NH2:1][C:2](=[N:20][OH:21])[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[CH2:6][N:7]([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH3:8].[CH3:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][N:24]1[C:29]1[CH:37]=[CH:36][C:32]([C:33]([OH:35])=O)=[CH:31][C:30]=1[C:38]([F:41])([F:40])[F:39]>>[CH3:8][N:7]([CH2:6][C:5]1[CH:17]=[CH:18][CH:19]=[C:3]([C:2]2[N:1]=[C:33]([C:32]3[CH:36]=[CH:37][C:29]([N:24]4[CH2:25][CH2:26][CH2:27][CH2:28][CH:23]4[CH3:22])=[C:30]([C:38]([F:41])([F:40])[F:39])[CH:31]=3)[O:21][N:20]=2)[CH:4]=1)[CH2:9][C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11].[CH3:8][N:7]([CH2:6][C:5]1[CH:17]=[CH:18][CH:19]=[C:3]([C:2]2[N:1]=[C:33]([C:32]3[CH:36]=[CH:37][C:29]([N:24]4[CH2:25][CH2:26][CH2:27][CH2:28][CH:23]4[CH3:22])=[C:30]([C:38]([F:40])([F:39])[F:41])[CH:31]=3)[O:35][N:20]=2)[CH:4]=1)[CH2:9][C:10]([OH:12])=[O:11]Participants
4
Reactant 2
Product 2
Procedure
Tert-butyl N-methyl-N-(3-{5-[4-(2-methylpiperidin-1-yl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}benzyl)glycinate was prepared following the general procedure 7 starting from Intermediate 21 and Intermediate 4. It was hydrolyzed following procedure 8, affording the title compound as a white powder. 1H NMR (DMSO-d6, 300 MHz) δ 8.50-8.37 (m, 2H), 8.32 (br s, 1H), 8.21 (d, J=7.4 Hz, 1H), 7.88 (d, J=8.6 Hz, 1H), 7.82-7.67 (m, 2H), 4.47 (s, 2H), 4.09 (s, 2H), 3.18 (m, 1H), 3.03-2.91 (m, 1H), 2.80 (s, 3H), 2.69-2.57 (m, 1H). 1.89-1.16 (m, 6H), 0.79 (d, J=6.1 Hz, 3H). LC/MS (Method B): 487.4 (M−H)−, 489.4 (M+H)+. HPLC (Method A) Rt 5.10 min (Purity: 100%).
Sources & evidence
- ORD record
- ord-590e014518a847f7b0b10fe9f09bc8ec
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815919B2
Reaction notes
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