Triethylamine → N-[4-(4-methylthiophenoxy)benzyl]-2,5-dimethylcyclopenta[1,2-c]pyrazole-3-carboxamide

HRID 257854Notes

Reaction equation

HRID 257854 reaction equation
[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([S:6][C:7]2[CH:14]=[CH:13][C:10]([CH2:11][NH2:12])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:24][N:25]1[C:29]([C:30](Cl)=[O:31])=[C:28]2[CH:33]=[C:34]([CH3:36])[CH:35]=[C:27]2[NH:26]1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([S:6][C:7]2[CH:14]=[CH:13][C:10]([CH2:11][NH:12][C:30]([C:29]3[N:25]([CH3:24])[NH:26][C:27]4=[CH:35][C:34]([CH3:36])=[CH:33][C:28]=34)=[O:31])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 435288314-(4-Methylthiophenoxy)benzylamineHCID 867473882,5-Dimethylcyclopenta[1,2-c]-pyrazole-3-carbonyl chloride

Product 1

HCID 131718252N-[4-(4-methylthiophenoxy)benzyl]-2,5-dimethylcyclopenta[1,2-c]pyrazole-3-carboxamideYield 69.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a stirred mixture of 4-(4-methylthiophenoxy)benzylamine (124 mg, 0.505 mM), triethylamine (61 mg, 0.60 mM) and toluene (20 ml) was added dropwise a solution (10 ml) of 2,5-dimethylcyclopenta[1,2-c]-pyrazole-3-carbonyl chloride(100 mg, 0.503 mM) in toluene at 0°-10° C., and the mixture was stirred for 3 h at the room temperature. The mixture was poured into ice water, and the mixture was extracted with toluene. The extract was washed with saturated sodium hydrogen carbonate solution, water, saturated ammonium chloride solution and brine, dried with magnesium sulfate, and concentrated in vacuo. The residue was chromatographed over silica gel to give N-[4-(4-methylthiophenoxy)benzyl]-2,5-dimethylcyclopenta[1,2-c]pyrazole-3-carboxamide (138 mg, 67%) as colorless crystals, m.p. 138.0° C.

Workup

  1. extractionthe mixture was extracted with toluene
  2. washThe extract was washed with saturated sodium hydrogen carbonate solution, water, saturated ammonium chloride solution and brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-8cd50ba80a504b4ab884f6bbdee456f1
Source dataset
uspto-grants-1993_11
Patent number
US05264448

Reaction notes

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