2,2'-Dimethyl-[1,1'-biphenyl]-4-carboxylic acid → Methyl 2-chloro-4-[5-(2,2'-dimethylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]benzoate

HRID 219942Notes

Reaction equation

HRID 219942 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17].[NH2:18][C:19](=[N:31]O)[C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:22]([Cl:30])[CH:21]=1>>[Cl:30][C:22]1[CH:21]=[C:20]([C:19]2[N:18]=[C:8]([C:6]3[CH:5]=[CH:4][C:3]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[CH3:17])=[C:2]([CH3:1])[CH:7]=3)[O:10][N:31]=2)[CH:29]=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25]

Participants

3

Reactant 2

HCID 219373032,2'-Dimethyl-[1,1'-biphenyl]-4-carboxylic acidHCID 72307499Methyl 4-[amino(hydroxyimino)methyl]-2-chlorobenzoate

Product 1

HCID 67528555Methyl 2-chloro-4-[5-(2,2'-dimethylbiphenyl-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 3 (113.14 mg; 0.50 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: 9.5/0.5), affording the title compound as an off-white solid. LC/MS (Method B): 419.3 (M−H)−, 460.3 (M+ACN)+. HPLC (Method A) Rt 6.51 min (Purity: 99.8%).

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: 9.5/0.5)

Sources & evidence

ORD record
ord-c3130d8708e145e490e215c689b6ffc7
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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