2'-Ethyl-2-(methoxymethyl)-[1,1'-biphenyl]-4-carboxylic acid → Methyl 4-{5-[2'-ethyl-2-(methoxymethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoate

HRID 219952Notes

Reaction equation

HRID 219952 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:34][OH:35])[C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[C:25]([F:33])[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:35][N:34]=[C:22]([C:23]3[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[C:25]([F:33])[CH:24]=3)[N:21]=2)=[CH:11][C:10]=1[CH2:18][O:19][CH3:20])[CH3:2]

Participants

3

Reactant 2

HCID 594958092'-Ethyl-2-(methoxymethyl)-[1,1'-biphenyl]-4-carboxylic acidHCID 76644654Methyl 4-[amino(hydroxyimino)methyl]-2-fluorobenzoate

Product 1

HCID 25255376Methyl 4-{5-[2'-ethyl-2-(methoxymethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoate

Procedure

The title compound was prepared following procedure described for example 35, step 1, but starting from Intermediate 36 (1 135.37 mg; 4.20 mmol) and Intermediate 1 (891.15 mg; 4.20 mmol). The reaction mixture was cooled to RT and concentrated affording yellow oil. It was precipitating in ACN. Solvent were removed and the solid was washed with MeOH, filtered off and dried under vacuum to afford the title compound as a white powder. 1H NMR (CDCl3) δ 8.43 (s, 1H), 8.18-7.99 (m, 4H), 7.41-7.35 (m, 3H), 7.29-7.24 (m, 1H), 7.11 (d, J=7.2 Hz, 1H), 4.27-4.17 (m, 2H), 3.98 (s, 3H), 3.34 (s, 3H), 2.50-2.28 (m, 2H), 1.05 (t, J=7.5 Hz, 3H). LC/MS (Method B): 447.2 (M+H)+. HPLC (Method A) Rt 6.14 min (Purity: 99.5%).

Workup

  1. customThe title compound was prepared following procedure
  2. concentrationconcentrated
  3. customaffording yellow oil
  4. customIt was precipitating in ACN
  5. customSolvent were removed
  6. washthe solid was washed with MeOH
  7. filtrationfiltered off
  8. customdried under vacuum

Sources & evidence

ORD record
ord-1ffa2d1c8aa2442492c5ca0d374f975d
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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