HCID 178432944, compound → 3-(2,4-Dichlorophenyl)-7-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2,6-dimethyl pyrazolo[5,1-b]oxazole

HRID 1671308Notes

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:17][N:16]=[C:15]([CH3:18])[C:14]=1[N:19]1[C:23]([CH3:24])=[N:22][C:21]([CH3:25])=[N:20]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:17]2[N:16]=[C:15]([CH3:18])[C:14]([N:19]3[C:23]([CH3:24])=[N:22][C:21]([CH3:25])=[N:20]3)=[C:13]2[O:12][C:10]=1[CH3:11]

Participants

Conditions

Temperature: 85 °C

Procedure

To a dispersion of 1-(2,4-dichlorophenyl)-2-(4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-3-methyl-1H-pyrazol-5-yloxy)propan-1-one (120 mg, 0.304 mmol) in 1,2-dichloroethane (1.217 ml) is added titanium tetrachloride (0.080 ml, 0.73 mmol). The reaction mixture is heated to 85° C. for 4 hours and then left at RT overnight. The mixture is quenched carefully with sat. NH4Cl (50 ml) and extracted with EtOAc (2×50 ml). The combined organic extracts are washed with brine, dried over MgSO4 and concentrated in vacuo to afford a white solid. Purification by recrystallisation from EtOAc (˜3 ml) yields the title compound as a white crystalline solid; MS: m/z 376.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 7.95 (1H, d), 7.77 (1H, d), 7.69 (1H, d), 2.38 (3H, s), 2.30 (3H, s), 2.28 (3H, s), 2.12 (3H, s).

Workup

customThe mixture is quenched carefully with sat. NH4Cl (50 ml)
extractionextracted with EtOAc (2×50 ml)
washThe combined organic extracts are washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customto afford a white solid
customPurification
customby recrystallisation from EtOAc (˜3 ml)

Sources & evidence

ORD record: ord-81958923b7ba49dd87c645f84fc92bff
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07994203B2

Reaction notes

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