1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-(4-Chloro-phenyl)-1-(2-chloro-phenyl)-4-cyanomethyl-1H-pyrazole-3-carboxylic acid [1-(4-bromo-phenyl)-ethyl]-amide

HRID 1644880Notes

Reaction equation

HRID 1644880 reaction equation
CCN=C=NCCCN(C)C.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[N:22]=[C:21]([C:31](O)=[O:32])[C:20]=2[CH2:34][C:35]#[N:36])=[CH:15][CH:14]=1.C1C=CC2N(O)N=NC=2C=1.[Br:47][C:48]1[CH:53]=[CH:52][C:51]([CH:54]([NH2:56])[CH3:55])=[CH:50][CH:49]=1>ClCCl>[Br:47][C:48]1[CH:53]=[CH:52][C:51]([CH:54]([NH:56][C:31]([C:21]2[C:20]([CH2:34][C:35]#[N:36])=[C:19]([C:16]3[CH:15]=[CH:14][C:13]([Cl:12])=[CH:18][CH:17]=3)[N:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[N:22]=2)=[O:32])[CH3:55])=[CH:50][CH:49]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 911751-(4-Bromophenyl)ethylamineHCID 591463351-(2-chlorophenyl)-5-(4-chlorophenyl)-4-(cyanomethyl)-1H-pyrazole-3-carboxylic acid

Product 1

HCID 591463265-(4-Chloro-phenyl)-1-(2-chloro-phenyl)-4-cyanomethyl-1H-pyrazole-3-carboxylic acid [1-(4-bromo-phenyl)-ethyl]-amideYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

EDAC (386 mg, 2.00 mmol) was added to a stirred solution of [B1] (500 mg, 1.34 mmol) and HOBT (236 mg, 1.75 mmol) in dichloromethane (80 ml) at room temperature under argon. After 15 minutes 1-(4-bromo-phenyl)-ethylamine (322 mg, 1.61 mmol) was added and stirring continued for 16 hours. The mixture was washed with saturated aqueous sodium bicarbonate solution (3×) then with brine, dried over magnesium sulphate, filtered and evaporated in vacuo to give the title compound [C1] (655 mg, 1.18 mmol, 88%) as a foam.

Workup

  1. washThe mixture was washed with saturated aqueous sodium bicarbonate solution (3×)
  2. dry with materialwith brine, dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-8a63d3c435f5436caf340426bd0db8ce
Source dataset
uspto-grants-2012_02
Patent number
US08124634B2

Reaction notes

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