Triethylamine → N-[[5-(3,5-dichlorophenyl)sulfanyl-1-isopropyl-4-(4-pyridylmethyl)pyrazol-3-yl]methyl]methanesulfonamide

HRID 1862471Notes

Reaction equation

HRID 1862471 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH:15]([CH3:17])[CH3:16])[N:13]=[C:12]([CH2:18][NH2:19])[C:11]=2[CH2:20][C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH:15]([CH3:17])[CH3:16])[N:13]=[C:12]([CH2:18][NH:19][S:35]([CH3:34])(=[O:37])=[O:36])[C:11]=2[CH2:20][C:21]2[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 514443[5-(3,5-Dichlorophenyl)sulfanyl-1-isopropyl-4-(4-pyridylmethyl)pyrazol-3-yl]methanamine

Product 1

HCID 514445N-[[5-(3,5-dichlorophenyl)sulfanyl-1-isopropyl-4-(4-pyridylmethyl)pyrazol-3-yl]methyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution containing 35 mg of 5-(3,5-dichlorophenylthio)-1-isopropyl-4-[(4-pyridyl)methyl]-1H-pyrazole-3-methylamine in 3 ml of anhydrous dichloromethane at room temperature under nitrogen was treated with 0.024 ml of triethylamine and 0.007 ml of methane sulphonyl chloride. The mixture was stirred at room temperature for 0.5 h. The mixture was partitioned between dichloromethane and saturated sodium hydrogen carbonate then extracted three times. Combined extracts were washed with brine then dried over anhydrous magnesium sulphate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using methanol/dichloromethane (1:19) for the elution to give 21 mg of N-[[5-(3,5-dichlorophenylthio)-1-isopropyl-4-[(4-pyridyl)methyl]-1H-pyrazol-3-yl]methyl]methanesulfonamide as a brown solid. Mass spectrum (ESI) m/z 465 [M+H]+. 1H NMR (DMSO) 1.30 (d, 6H), 2.90 (s, 3H), 3.92 (s, 2H), 4.20 (d, 2H), 4.73 (m, 1H), 6.89 (s, 2H), 7.11 (d, 2H), 7.38 (s, 1H), 7.56 (t, 1H), 8.30 (d, 2H).

Workup

  1. customThe mixture was partitioned between dichloromethane and saturated sodium hydrogen carbonate
  2. extractionthen extracted three times
  3. washCombined extracts were washed with brine
  4. dry with materialthen dried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography on silica gel
  8. washfor the elution

Sources & evidence

ORD record
ord-73e3c0af02f54ee1bfdd10d96df48c1c
Source dataset
uspto-grants-2003_03
Patent number
US06538015B1

Reaction notes

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