HCID 6059119, compound → Methyl 3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzoate

HRID 219954Notes

Reaction equation

HRID 219954 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].[NH2:20]/[C:21](=[N:32]/O)/[C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=1)[C:25]([O:27][CH3:28])=[O:26]>>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:12][N:32]=[C:21]([C:22]3[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=3)[C:25]([O:27][CH3:28])=[O:26])[N:20]=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

Reactant 2

HCID 6059119HCID 6059119, compoundHCID 594958222-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid

Product 1

HCID 67541290Methyl 3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-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 28 (128.15 mg; 0.5 mmol) and methyl 3-[(E)-amino(hydroxyimino)methyl]benzoate, prepared as described in US2004/204461 from methyl 3-cynaobenzoate (Maybridge; RJC00610EA), (97 mg; 0.5 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 FC (c-hex/EtOAc: 9.5/0.5 to 5/5). It was then suspended in MeCN and filtrated, affording the title compound as a white solid. LC/MS (Method B): 415.2 (M+H)+. HPLC (Method A) Rt 6.48 min (Purity: 96.2%).

Workup

  1. customThe title compound was prepared following procedure
  2. customprepared
  3. filtrationThe reaction mixture was filtered through a SPE NH2 column (2 g)
  4. washrinsed with ACN
  5. washrinsed with ACN
  6. customAfter evaporation of the solvents
  7. customthe crude product was purified by FC (c-hex/EtOAc: 9.5/0.5 to 5/5)
  8. filtrationfiltrated

Sources & evidence

ORD record
ord-c1d0f4bbcf53434c91620ef2ac76ee39
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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