2-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid → 2-Chloro-4-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzoic acid
Reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([OH:12])=O)[CH:7]=[CH:6][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19].[NH2:20][C:21](=[N:33][OH:34])[C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]([Cl:32])[CH:23]=1>>[Cl:32][C:24]1[CH:23]=[C:22]([C:21]2[N:20]=[C:10]([C:8]3[CH:7]=[CH:6][C:5]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[CH3:19])=[C:4]([CH2:3][O:2][CH3:1])[CH:9]=3)[O:12][N:33]=2)[CH:31]=[CH:30][C:25]=1[C:26]([O:28][CH3:29])=[O:27].[Cl:32][C:24]1[CH:23]=[C:22]([C:21]2[N:20]=[C:10]([C:8]3[CH:7]=[CH:6][C:5]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[CH3:19])=[C:4]([CH2:3][O:2][CH3:1])[CH:9]=3)[O:34][N:33]=2)[CH:31]=[CH:30][C:25]=1[C:26]([OH:28])=[O:27]Participants
4
Reactant 2
Product 2
Procedure
Methyl 2-chloro-4-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzoate was prepared following the general procedure 7 starting from Intermediate 3 and Intermediate 34. It was then hydrolysed following procedure 9, affording the title compound as a white powder. 1H NMR (DMSO-d6, 300 MHz) δ 13.77 (br s, 1H), 8.34 (d, J=1.5 Hz, 1H), 8.20-8.15 (m, 3H), 8.02 (d, J=7.9 Hz, 1H), 7.43 (d, J=7.9 Hz, 1H), 7.37-7.27 (m, 3H), 7.15 (d, J=7.2 Hz, 1H), 4.25-4.14 (m, 2H), 3.25 (s, 3H), 2.04 (s, 3H). LC/MS (Method B): 433.2 (M−H)−, 435.2 (M+H)+. HPLC (Method A) Rt 5.35 min (Purity: 98.5%). CHN analysis: [C24H19N2O4Cl] Calculated: C, 66.29%; H, 4.40%; N, 6.44%; Cl, 8.15%. Found: C, 66.04%; H, 4.52%; N, 6.49%; Cl, 8.23%.
Sources & evidence
- ORD record
- ord-9434f44a3867481b992e9345b870b10f
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815919B2
Reaction notes
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