2'-Chloro-3'-fluoro-2-(methoxymethyl)biphenyl-4-carboxylic acid → Tert-butyl n-(4-{5-[2'-chloro-3'-fluoro-2-(methoxymethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzyl)-n-methylglycinate
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:41][OH:42])[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])=[C:25]([F:40])[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:41]=[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])([CH3:36])[CH3:35])=[O:31])=[C:25]([F:40])[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:42][N:41]=[C:22]([C:23]3[CH:39]=[CH:38][C:26]([CH2:27][N:28]([CH3:37])[CH2:29][C:30]([OH:32])=[O:31])=[C:25]([F:40])[CH:24]=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}-2-fluorobenzyl)-N-methylglycinate was prepared following the general procedure 3 starting from Intermediate 62 and Intermediate 32. It was hydrolyzed following general procedure 8 to afford the title compound as a white powder. 1H NMR (DMSO-d6, 300 MHz) δ 8.36 (brs, 1H), 8.23 (m, 1H), 8.08 (m, 1H), 8.00 (m, 1H), 7.89 (m, 1H), 7.54 (m, 3H), 7.26 (m, 1H), 4.48 (brs, 2H), 4.28 (m, 2H), 4.12 (brs, 2H), 3.25 (s, 3H), 2.80 (s, 3H). LC/MS (Method B): 514.1 (M+H)+, 512.2 (M−H)−. HPLC (Method A) Rt 3.90 min (Purity: 100%).
Sources & evidence
- ORD record
- ord-1a8c5daa4e1b4a64baaf67b7d5097d0b
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815919B2
Reaction notes
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