2-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid → 5-[2-(Methoxymethyl)-2'-methylbiphenyl-4-yl]-3-[3-(methylsulfonyl)phenyl]-1,2,4-oxadiazole
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].O[N:21]=[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([S:30]([CH3:33])(=[O:32])=[O:31])[CH:25]=1)[NH2:23]>>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:12][N:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([S:30]([CH3:33])(=[O:32])=[O:31])[CH:25]=3)[N:21]=2)[CH:7]=[CH:6][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19]Participants
3
Procedure
The title compound was obtained following procedure described for example 54 step 1 but starting from Intermediate 28 (112 mg; 0.44 mmol) and Intermediate 64 (197 mg; 0.44 mmol). Purification by column chromatography (EtOAc:cHex from 10:90 to 50:50) yielded to a colorless oil. Trituration in ACN/pentane followed by filtration gave the title compound as an off-white powder. 1H NMR (DMSO-d6, 300 MHz) δ 8.59 (t, J=1.7 Hz, 1H), 8.47 (m, 1H), 8.35 (d, J=1.7 Hz, 1H), 8.21 (m, 2H), 7.93 (t, J=8.0 Hz, 1H), 7.44 (d, J=8.0 Hz, 1H), 7.33 (m, 3H), 7.15 (d, J=7.1 Hz, 1H), 4.23 (d, J=13.8 Hz, 1H), 4.17 (d, J=13.8 Hz, 1H), 3.35 (s, 3H), 3.26 (s, 3H), 2.04 (s, 3H). LC/MS (Method B): 435.3 (M+H)+. HPLC (Method A) Rt 5.35 min (Purity: 97.6%).
Workup
- customPurification by column chromatography (EtOAc:cHex from 10:90 to 50:50)
- customyielded to a colorless oil
- filtrationTrituration in ACN/pentane followed by filtration
Sources & evidence
- ORD record
- ord-d520ae36765b45fcaede3a28d5ff37e4
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202865B2
Reaction notes
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