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Triethylamine → N-{2-[4-(3,5-Dichlorobenzyl)-3,5-diethyl-I H-pyrazol-1-yl]ethyl}-1-methyl-1H-imidazole-4-sulfonamide

HRID 353078
Notes
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Reaction equation

HRID 353078 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[CH2:5][C:6]1[C:7]([CH2:16][CH3:17])=[N:8][N:9]([CH2:13][CH2:14][NH2:15])[C:10]=1[CH2:11][CH3:12].[CH3:22][N:23]1[CH:27]=[C:26]([S:28](Cl)(=[O:30])=[O:29])[N:25]=[CH:24]1.C(N(CC)CC)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[CH2:5][C:6]1[C:7]([CH2:16][CH3:17])=[N:8][N:9]([CH2:13][CH2:14][NH:15][S:28]([C:26]2[N:25]=[CH:24][N:23]([CH3:22])[CH:27]=2)(=[O:30])=[O:29])[C:10]=1[CH2:11][CH3:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27368871-methyl-1H-imidazole-4-sulfonyl chlorideHCID 99233572-[4-(3,5-Dichlorobenzyl)-3,5-diethyl-1h-pyrazol-1-yl]ethanamine

Product 1

HCID 10183664N-{2-[4-(3,5-Dichlorobenzyl)-3,5-diethyl-I H-pyrazol-1-yl]ethyl}-1-methyl-1H-imidazole-4-sulfonamideYield 39%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

A solution of the amine of Example 43 (98 mg, 0.30 mmol) in dimethylformamide (3.75 ml) was treated with 1-methylimidazole-4-sulphonyl chloride (60 mg, 0.33 mmol) and triethylamine (46 μL, 0.33 mmol) and the resulting mixture was stirred at room temperature for 18 hours. The solution was concentrated under reduced pressure. The residue was partitioned between dichloromethane and saturated aqueous sodium hydrogencarbonate solution. The organic extract was dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (95:5, by volume) to afford the title compound (55 mg) as a white solid, m.p. 172-174° C.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customThe residue was partitioned between dichloromethane and saturated aqueous sodium hydrogencarbonate solution
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (95:5, by volume)

Sources & evidence

ORD record
ord-4c89d6dabf5f4b568460f9241d3ee33b
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06750230B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes