Imidazole → HCID 54172019, compound

HRID 2301368Notes

Reaction equation

[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH2:9][C:10]1[N:14]([C:15]2[C:20]([Cl:21])=[CH:19][C:18]([C:22]([F:25])([F:24])[F:23])=[CH:17][C:16]=2[Cl:26])[N:13]=[C:12]([CH:27]=[N:28][OH:29])[C:11]=1[S:30]([CH3:32])=[O:31].N1C=CN=C1.O>CN(C)C=O>[Si:1]([O:29][N:28]=[CH:27][C:12]1[C:11]([S:30]([CH3:32])=[O:31])=[C:10]([NH2:9])[N:14]([C:15]2[C:20]([Cl:21])=[CH:19][C:18]([C:22]([F:25])([F:23])[F:24])=[CH:17][C:16]=2[Cl:26])[N:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of tert-butyldimethylsilyl chloride (0.8 g) in N,N-dimethylformamide (DMF) was added to a stirred solution of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde oxime (2.0 g) in (DMF), followed by dropwise addition of a solution of imidazole (0.72 g) in DMF during 7-minutes. The mixture was heated at 50° C. for 3.5-hours and then held at 20° C. for 18 hours. The mixture was diluted (water), extracted (methyl tert-butyl ether) and the organic phase washed in turn with NaHCO3 solution, 5% HCl solution and with NaHCO3 solution, dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel to give 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde O-(tert-butyldimethylsilyl)oxime (0.76 g)as a light yellow solid m.p.150-154° C. Compound 21.

Workup

extractionextracted (methyl tert-butyl ether)
washthe organic phase washed in turn with NaHCO3 solution, 5% HCl solution and with NaHCO3 solution
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated
customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-bdb227d76ca04d838885e42c6128f78a
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06500850B2

Reaction notes

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