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

HRID 219957Notes

Reaction equation

HRID 219957 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:23]=[CH:24][C:25]([Cl:32])=[C:26]([CH:31]=1)[C:27]([O:29][CH3:30])=[O:28]>>[Cl:32][C:25]1[CH:24]=[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][C:26]=1[C:27]([O:29][CH3:30])=[O:28]

Participants

3

Reactant 2

HCID 594958222-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acidHCID 72307491Methyl 5-[amino(hydroxyimino)methyl]-2-chlorobenzoate

Product 1

HCID 67528893Methyl 2-chloro-5-{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 (461.34 mg; 1.80 mmol) and Intermediate 54 (342.95 mg; 1.50 mmol). The reaction mixture was filtered through a SPE NH2 column (10 g) and rinsed with ACN. The filtrate was passed through a SPE SCX column (10 g) and rinsed with ACN. After evaporation of the solvents, the crude product was purified by flash chromatography (c-hex/(DCM/EtOAc 1:1) gradient from 1:0 to 1:1), affording the title compound as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 8.68 (d, J=2.1 Hz, 1H), 8.43 (d, J=1.1 Hz, 1H), 8.25 (dd, J=8.3, 2.1 Hz, 1H), 8.17 (dd, J=7.9, 1.7 Hz, 1H), 7.62 (d, J=8.4 Hz, 1H), 7.36-7.24 (m, 4H), 7.13 (d, J=7.2 Hz, 1H), 4.28-4.19 (m, 2H), 4 (s, 3H), 3.34 (s, 3H), 2.08 (s, 3H). LC/MS (Method B): 449.1 (M+H)+. HPLC (Method A) Rt 6.10 min (Purity: 96.0%).

Workup

  1. customThe title compound was prepared following procedure
  2. filtrationThe reaction mixture was filtered through a SPE NH2 column (10 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/(DCM/EtOAc 1:1) gradient from 1:0 to 1:1)

Sources & evidence

ORD record
ord-a9989e224ffe43409d5f4abbb3d26d3b
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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