2-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid → Methyl 2-chloro-4-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzoate

HRID 219943Notes

Reaction equation

HRID 219943 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:33]O)[C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]([Cl:32])[CH:23]=1>>[Cl:32][C:24]1[CH:23]=[C:22]([C:21]2[N:20]=[C:10]([C:8]3[CH:7]=[CH:6][C:5]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[CH3:19])=[C:4]([CH2:3][O:2][CH3:1])[CH:9]=3)[O:12][N:33]=2)[CH:31]=[CH:30][C:25]=1[C:26]([O:28][CH3:29])=[O:27]

Participants

3

Reactant 2

HCID 594958222-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acidHCID 72307499Methyl 4-[amino(hydroxyimino)methyl]-2-chlorobenzoate

Product 1

HCID 66678050Methyl 2-chloro-4-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzoateYield 82%

Procedure

The title compound was prepared following procedure described for example 35, step 1, but starting from Intermediate 28 (1 076.46 mg; 4.20 mmol) and Intermediate 34 (960.27 mg; 4.20 mmol). The reaction mixture was cooled to RT and concentrated affording a brownish oil which was washed with MeOH (20 mL) affording a suspension that was filtered affording the title compound as a beige solid (1.5 g; 82%). 1H NMR (DMSO-d6, 300 MHz) δ 8.34 (d, J=1.5 Hz, 1H), 8.23 (d, J=1.3 Hz, 1H), 8.21 (dd, J=3.6, 1.7 Hz, 1H), 8.18 (dd, J=3.5, 1.8 Hz, 1H), 8.06 (d, J=8.0 Hz, 1H), 7.44 (d, J=7.9 Hz, 1H), 7.37-7.27 (m, 3H), 7.15 (d, J=7.0 Hz, 1H), 4.23 (d, J=12.8 Hz, 1H), 4.16 (d, J=12.8 Hz, 1H), 3.92 (s, 3H), 3.25 (s, 3H), 2.04 (s, 3H). LC/MS (Method B): 449.1 (M+H)+. HPLC (Method A) Rt 6.14 min (Purity: 97.6%).

Workup

  1. customThe title compound was prepared following procedure
  2. concentrationconcentrated
  3. customaffording a brownish oil which
  4. washwas washed with MeOH (20 mL)
  5. customaffording a suspension that
  6. filtrationwas filtered

Sources & evidence

ORD record
ord-28d511104d1342cabc542c80ca56fb9e
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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