2'-Methyl-2-[(methylsulfonyl)methyl]biphenyl-4-carboxylic acid → Methyl 2-chloro-4-(5-{2'-methyl-2-[(methylsulfonyl)methyl]biphenyl-4-yl}-1,2,4-oxadiazol-3-yl)benzoate

HRID 219953Notes

Reaction equation

HRID 219953 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14](O)=O)=[CH:10][C:9]=1[CH2:17][S:18]([CH3:21])(=[O:20])=[O:19].[NH2:22][C:23](=[N:35][OH:36])[C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[C:26]([Cl:34])[CH:25]=1>>[Cl:34][C:26]1[CH:25]=[C:24]([C:23]2[N:22]=[C:14]([C:11]3[CH:12]=[CH:13][C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[CH3:1])=[C:9]([CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:10]=3)[O:36][N:35]=2)[CH:33]=[CH:32][C:27]=1[C:28]([O:30][CH3:31])=[O:29]

Participants

3

Reactant 2

HCID 594956542'-Methyl-2-[(methylsulfonyl)methyl]biphenyl-4-carboxylic acidHCID 72307499Methyl 4-[amino(hydroxyimino)methyl]-2-chlorobenzoate

Product 1

HCID 67529753Methyl 2-chloro-4-(5-{2'-methyl-2-[(methylsulfonyl)methyl]biphenyl-4-yl}-1,2,4-oxadiazol-3-yl)benzoate

Procedure

The title compound was prepared following procedure described for example 4, step 1, but starting from Intermediate 40 (182.62 mg; 0.60 mmol) and Intermediate 34 (114.32 mg; 0.50 mmol). The reaction mixture was filtered through a SPE NH2 column (2 g) and rinsed with ACN. The filtrate was passed through a SPE SCX column (2 g) and rinsed with ACN. After evaporation of the solvents, the crude product was purified by flash chromatography (c-hex/EtOAc: 1/1), affording the title compound. 1H NMR (CDCl3) δ 8.58 (d, J=1.7 Hz, 1H), 8.32 (d, J=1.5 Hz, 1H), 8.28 (dd, J=8.0, 1.8 Hz, 1H), 8.15 (dd, J=8.1, 1.6 Hz, 1H), 7.98 (d, J=8.1 Hz, 1H), 7.48 (d, J=7.9 Hz, 1H), 7.41-7.29 (m, 3H), 7.20 (d, J=7.3 Hz, 1H), 4.33 (d, J=13.9 Hz, 1H), 4.19 (d, J=14.0 Hz, 1H), 3.98 (s, 3H), 2.64 (s, 3H), 2.09 (s, 3H). LC/MS (Method B): 495.2 (M−H)−, 497.1 (M+H)+. HPLC (Method A) Rt 5.51 min (Purity: 99.6%).

Workup

  1. customThe title compound was prepared following procedure
  2. filtrationThe reaction mixture was filtered through a SPE NH2 column (2 g)
  3. washrinsed with ACN
  4. washrinsed with ACN
  5. customAfter evaporation of the solvents
  6. customthe crude product was purified by flash chromatography (c-hex/EtOAc: 1/1)

Sources & evidence

ORD record
ord-365f1348dd714105abe50087ce589ee0
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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