Diethylamine → HCID 44479603, compound

HRID 2067968Notes

Reaction equation

HRID 2067968 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:13][C:14]([C:16]2[CH:17]=[N:18][N:19]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=3)[C:20]=2[CH3:21])=[O:15])[CH2:9][C:10](Cl)=[O:11])[CH:5]=[CH:6][CH:7]=1.[CH2:30]([NH:32][CH2:33][CH3:34])[CH3:31]>ClCCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:13][C:14]([C:16]2[CH:17]=[N:18][N:19]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=3)[C:20]=2[CH3:21])=[O:15])[CH2:9][C:10](=[O:11])[N:32]([CH2:33][CH3:34])[CH2:30][CH3:31])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 58443402HCID 58443402, compound

Product 1

HCID 44479603HCID 44479603, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution 3-(3-bromo-phenyl)-3-{[1-(3,4-dichloro-phenyl)-5-methyl-1H-pyrazole-4-carbonyl]-amino}-propionyl chloride (100 mg, 0.19 mmol) in 1,2-dichloroethane (3 mL) is treated with diethylamine (28 mg, 0.38 mmol) in one portion and stirred at room temperature for 2 hours. The reaction mixture is concentrated in vacuo and purified by flash chromatography on silica gel (eluted with 1 to 4% MeOH/CH2Cl2) to afford 1-(3,4-dichloro-phenyl)-5-methyl-1H-pyrazole-4-carboxylic acid [1-(3-bromo-phenyl)-2-diethylcarbamoyl-ethyl]-amide as a white foam (6.0 mg, 6.0%).

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. custompurified by flash chromatography on silica gel (eluted with 1 to 4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-18691adf96634e2182d0562351677e67
Source dataset
uspto-grants-2012_10
Patent number
US08293917B2

Reaction notes

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