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

HRID 377639
Notes
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Reaction equation

HRID 377639 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 70254974N-(Piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-hydroxy-methylpyrazole-3-carboxamideHCID 86605672Diethylaminosulfide trifluoride

Product 1

HCID 70255079N-(Piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-fluoro-methylpyrazole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

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

  1. extractionextracted with DCM
  2. washwashed with saturated NaCl solution
  3. dry with materialdried over MgSO4
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes