Sodium Bicarbonate → N-(Piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-fluoro-methylpyrazole-3-carboxamide

HRID 377639Notes

Reaction equation

[N:1]1([N:7]([CH3:31])[C:8]([C:10]2[C:14](O)=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[N:12]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=3[Cl:30])[N:11]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F-:32].[F-].[F-].C(N(SN(CC)CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[N:1]1([N:7]([CH3:31])[C:8]([C:10]2[C:14]([F:32])=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[N:12]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=3[Cl:30])[N:11]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 600 mg of the compound of EXAMPLE 1 in 24 ml of DCM is added dropwise to a solution of 0.19 ml of diethylamino sulfide trifluoride in 24 ml of DCM at -78° C. under nitrogen. The mixture is allowed to warm up slowly to 0° C. and then stirred for one hour at 0° C. The reaction mixture is poured into saturated NaHCO3 solution and then extracted with DCM, washed with saturated NaCl solution and dried over MgSO4. The residue is chromatographed on fine silica using AcOEt/toluene (5/95 to 40/60; v/v) as the eluent to give 250 mg of the expected product, m.p.=184° C.

Workup

extractionextracted with DCM
washwashed with saturated NaCl solution
dry with materialdried over MgSO4
customThe residue is chromatographed on fine silica

Sources & evidence

ORD record: ord-3f7e5f7639ab4c34956f2e4ce1dea312
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06028084

Reaction notes

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