HCID 178434687, compound → 3-(2,4-Dichloro-phenyl)-7-(3-trifluoromethyl-pyrazol-1-yl)-2,6-dimethyl-pyrazolo[5,1-b]oxazole

HRID 1671306Notes

Reaction equation

HRID 1671306 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)[CH:10]([O:12][C:13]1[NH:14][N:15]=[C:16]([CH3:27])[C:17]=1[N:18]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[N:19]1)[CH3:11]>ClCCCl.[Ti](Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[N:15]=[C:16]([CH3:27])[C:17]([N:18]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[N:19]3)=[C:13]2[O:12][C:10]=1[CH3:11]

Participants

4

Reactant 1

HCID 178434687HCID 178434687, compound

Product 1

HCID 448165913-(2,4-Dichloro-phenyl)-7-(3-trifluoromethyl-pyrazol-1-yl)-2,6-dimethyl-pyrazolo[5,1-b]oxazole

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
85 °C

Procedure

1-(2,4-Dichloro-phenyl)-2-(5′-methyl-3-trifluoromethyl-2′H-[1,4′]bipyrazolyl-3′-yloxy)-propan-1-one (150 mg, 0.346 mmol) is dissolved in 1,2-dichloroethane (1.39 ml) and titanium tetrachloride (0.046 ml, 0.416 mmol) is added; the reaction mixture is stirred at 85° C. under N2 for 3 hours. The reaction mixture is allowed to cool to RT and quenched with sat. ammonium chloride then added to a further 50 ml solution of ammonium chloride. The crude product is extracted with EtOAc (2×50 ml). The combined organics are washed with water, brine, dried over MgSO4 and concentrated in vacuo. Purification of the crude product by ISCO combiflash chromatography, eluting with 0 to 100% (EtOAc/Iso-hexane) on a 24 g SiO2-column afford the title compound as a solid MS: m/z 415.25 [M+H]+; 1H NMR (400.13 MHz (CDCl3) δ 7.69 (1H, dd), 7.60 (1H, d), 7.54 (1H, d), 7.43 (1H, dd), 6.72 (1H, d), 2.37 (3H, s), 2.35 (3H, s).

Workup

  1. temperatureto cool to RT
  2. customquenched with sat. ammonium chloride
  3. additionthen added to a further 50 ml solution of ammonium chloride
  4. extractionThe crude product is extracted with EtOAc (2×50 ml)
  5. washThe combined organics are washed with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude product by ISCO combiflash chromatography
  9. washeluting with 0 to 100% (EtOAc/Iso-hexane) on a 24 g SiO2-column

Sources & evidence

ORD record
ord-17461bb34dd64c109c1c4a7e6922366a
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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