Formaldehyde → HCID 12018681, compound

HRID 1860520Notes

Reaction equation

HRID 1860520 reaction equation
[C:1]1([CH3:30])[CH:6]=[CH:5][C:4]([N:7]2[C:11](N)=[CH:10][C:9]([C:13]3[CH:18]=[CH:17][C:16]([NH:19][S:20]([C:23]4[CH:28]=[CH:27]C(N)=C[CH:24]=4)(=[O:22])=[O:21])=[CH:15][CH:14]=3)=[N:8]2)=[CH:3][CH:2]=1.[CH2:31]=O.O.[BH3-][C:35]#[N:36].[Na+].[C:38](#[N:40])[CH3:39]>C(O)(=O)C.C([O-])(O)=O.[Na+]>[CH3:31][NH:40][C:38]1[CH:27]=[CH:28][C:23]([S:20]([NH:19][C:16]2[CH:15]=[CH:14][C:13]([C:9]3[CH:10]=[C:11]([NH:36][CH3:35])[N:7]([C:4]4[CH:3]=[CH:2][C:1]([CH3:30])=[CH:6][CH:5]=4)[N:8]=3)=[CH:18][CH:17]=2)(=[O:22])=[O:21])=[CH:24][CH:39]=1

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 962WaterHCID 6342AcetonitrileHCID 5003444Sodium cyanoborohydrideHCID 12018680HCID 12018680, compound

Product 1

HCID 12018681HCID 12018681, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 1-(4-tolyl)-3-(4′-(4-aminophenyl)sulfonylamino phenyl)-5-aminopyrazole (0.07 g, 0.34 mmol) in acetonitrile (5 mL) at room temperature was added 37% formaldehyde in H2O (0.028 mL, 0.34 mmol), acetic acid (0.01 mL) and NaCNBH3 (0.02 g, 0.34 mmol). The mixture was stirred at room temperature overnight. The mixture was diluted with saturated aqueous NaHCO3 solution (10 mL) and extracted with EtOAc (50 mL). The organic layer was separated, dried over Na2SO4 and concentrated. The residue was purified by column chromatography, eluting with 1:1 hexanes/EtOAc to give 4-(methylamino)-N-[4-[5-(methylamino)-1-(4-methylphenyl)-1H-pyrazol-3-yl]phenyl]-benzensulfonamide.

Workup

  1. extractionextracted with EtOAc (50 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography
  6. washeluting with 1:1 hexanes/EtOAc

Sources & evidence

ORD record
ord-d6188f6c32fd46eaa72c0f76780489a7
Source dataset
uspto-grants-2003_03
Patent number
US06531478B2

Reaction notes

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