p-Toluenesulfonyl isocyanate → N-[({2-[4-(3,5-dimethyl-4-phenyl-1H-pyrazol-1-yl)phenyl]ethyl}amino)carbonyl]-4-methylbenzenesulfonamide

HRID 891081Notes

Reaction equation

HRID 891081 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:5]([CH3:13])[N:4]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH2:22])=[CH:16][CH:15]=2)[N:3]=1.[C:23]1([CH3:35])[CH:28]=[CH:27][C:26]([S:29]([N:32]=[C:33]=[O:34])(=[O:31])=[O:30])=[CH:25][CH:24]=1>ClCCl>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[C:5]([CH3:13])[N:4]([C:14]2[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][NH:22][C:33]([NH:32][S:29]([C:26]3[CH:27]=[CH:28][C:23]([CH3:35])=[CH:24][CH:25]=3)(=[O:31])=[O:30])=[O:34])=[CH:18][CH:19]=2)[N:3]=1

Participants

4

Reactant 2

HCID 77703p-Toluenesulfonyl isocyanateHCID 222446652-[4-(3,5-Dimethyl-4-phenyl-1H-pyrazol-1-yl)phenyl]ethylamine

Product 1

HCID 10239013N-[({2-[4-(3,5-dimethyl-4-phenyl-1H-pyrazol-1-yl)phenyl]ethyl}amino)carbonyl]-4-methylbenzenesulfonamideYield 39.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[4-(3,5-dimethyl-4-phenyl-1H-pyrazol-1-yl)phenyl]ethylamine (step 3, 166 mg, 0.57 mmol) in dichloromethane (10 ml) was added p-toluenesulfonyl isocyanate (135 mg, 0.68 mmol). The resulting mixture was stirred at room temperature for 30 min. The reaction mixture washed with water and the organic phase was dried (Na2SO4). After removal of the solvent, the crude product was purified by TLC with dichloromethane/methanol (10:1) to afford 110 mg (39%) of the title compound as yellow solids: MS (ESI) m/z 489 [M+H]+, 487 [M−H]−, 1H-NMR (CDCl3) δ 7.77 (2H, d, J=8.0 Hz), 7.45-7.16 (11H, m), 6.54 (1H, br.s), 3.36 (2H, br.s), 2.73 (2H, br.s), 2.31 (3H, s), 2.28 (3H, s), 2.20 (3H, s).

Workup

  1. washThe reaction mixture washed with water
  2. dry with materialthe organic phase was dried (Na2SO4)
  3. customAfter removal of the solvent
  4. customthe crude product was purified by TLC with dichloromethane/methanol (10:1)

Sources & evidence

ORD record
ord-2b60a62e4f3d4b108dc9aa65743ae40c
Source dataset
uspto-grants-2006_02
Patent number
US07001917B2

Reaction notes

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