2'-Ethyl-2-(methoxymethyl)-[1,1'-biphenyl]-4-carboxylic acid → N-(4-{5-[2'-ethyl-2-(methoxymethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoyl)-beta-alanine

HRID 2410574Notes

Reaction equation

HRID 2410574 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15](O)=O)=[CH:11][C:10]=1[CH2:18][O:19][CH3:20])[CH3:2].[NH2:21][C:22](=[N:40][OH:41])[C:23]1[CH:38]=[CH:37][C:26]([C:27]([NH:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:28])=[C:25]([F:39])[CH:24]=1>>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:41][N:40]=[C:22]([C:23]3[CH:38]=[CH:37][C:26]([C:27]([NH:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:28])=[C:25]([F:39])[CH:24]=3)[N:21]=2)=[CH:11][C:10]=1[CH2:18][O:19][CH3:20])[CH3:2].[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:41][N:40]=[C:22]([C:23]3[CH:38]=[CH:37][C:26]([C:27]([NH:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[O:28])=[C:25]([F:39])[CH:24]=3)[N:21]=2)=[CH:11][C:10]=1[CH2:18][O:19][CH3:20])[CH3:2]

Participants

4

Reactant 2

HCID 594958092'-Ethyl-2-(methoxymethyl)-[1,1'-biphenyl]-4-carboxylic acidHCID 86661513ethyl N-{4-[amino(hydroxyimino)methyl]-2-fluorobenzoyl}-beta-alaninate

Product 2

HCID 58066278N-(4-{5-[2'-ethyl-2-(methoxymethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoyl)-beta-alanineHCID 66678186Ethyl N-(4-{5-[2'-ethyl-2-(methoxymethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoyl)-beta-alaninate

Procedure

Ethyl N-(4-{5-[2′-ethyl-2-(methoxymethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoyl)-beta-alaninate was prepared following the general procedure 3 starting from Intermediate 7 and Intermediate 6. It was hydrolyzed following the general procedure 9 affording the title compound as a white powder. 1H NMR (DMSO-d6, 300 MHz) δ 12.31 (s, 1H), 8.61-8.55 (m, 1H), 8.33 (d, J=1.8 Hz, 1H), 8.17 (dd, J=7.9, 1.8 Hz, 1H), 8.03 (dd, J=8.0, 1.5 Hz, 1H), 7.95 (dd, J=10.7, 1.5 Hz, 1H), 7.84 (t, J=7.6 Hz, 1H), 7.45 (d, J=8.0 Hz, 1H), 7.41 (s, 1H), 7.39 (s, 1H), 7.34-7.26 (m, 1H), 7.12 (d, J=7.5 Hz, 1H), 4.23 (d, J=12.8 Hz, 1H), 4.14 (d, J=12.8 Hz, 1H), 3.49 (m, 2H), 3.25 (s, 3H), 2.53 (t, J=6.8 Hz, 2H), 2.47-2.19 (m, 2H), 0.99 (t, J=7.5 Hz, 3H). LC/MS (Method B): 502.4 (M−H)−, 504.4 (M+H)+. HPLC (Method A) Rt 5.03 min (Purity: 97.4%).

Sources & evidence

ORD record
ord-7fa26240f2bd40888b0c1fbe85b9f3e1
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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