2'-Chloro-3'-fluoro-2-(methoxymethyl)biphenyl-4-carboxylic acid → HCID 131731806, compound
Reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([OH:17])=O)=[CH:11][C:10]=1[CH2:18][O:19][CH3:20].[NH2:21][C:22](=[N:40][OH:41])[C:23]1[CH:39]=[CH:38][C:26]([CH2:27][N:28]([CH3:37])[CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:25][CH:24]=1>>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:17][N:40]=[C:22]([C:23]3[CH:39]=[CH:38][C:26]([CH2:27][N:28]([CH3:37])[CH2:29][C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])=[CH:25][CH:24]=3)[N:21]=2)=[CH:11][C:10]=1[CH2:18][O:19][CH3:20].[ClH:1].[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:41][N:40]=[C:22]([C:23]3[CH:24]=[CH:25][C:26]([CH2:27][N:28]([CH3:37])[CH2:29][C:30]([OH:32])=[O:31])=[CH:38][CH:39]=3)[N:21]=2)=[CH:11][C:10]=1[CH2:18][O:19][CH3:20]Participants
4
Reactant 2
Product 2
Procedure
Tert-butyl N-(4-{5-[2′-chloro-3′-fluoro-2-(methoxymethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methylglycinate was prepared following the general procedure 3 starting from Intermediate 62 and Intermediate 31. It was hydrolyzed following general procedure 8 to afford the title compound as a white powder (326 mg, 80%). 1H NMR (DMSO-d6, 300 MHz) δ 8.35 (brs, 1H), 8.22 (m, 3H), 7.81 (d, J=8.4 Hz, 2H), 7.59-7.48 (m, 3H), 7.26 (m, 1H), 4.48 (brs, 2H), 4.28 (m, 2H), 4.11 (brs, 2H), 3.25 (s, 3H), 2.81 (s, 3H). LC/MS (Method B): 496.1 (M+H)+, 494.2 (M−H)−. HPLC (Method A) Rt 3.96 min (Purity: 100%).
Sources & evidence
- ORD record
- ord-1a68c7c126764ee79249a2632498b14b
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815919B2
Reaction notes
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