Isopropylamine → 1-(2-Chloro-phenyl)-5-(4-chloro-phenyl)-4-(isopropylamino-methyl)-1H-pyrazole-3-carboxylic acid ethyl ester

HRID 1294841Notes

Reaction equation

HRID 1294841 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH2:11]Br)=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[N:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[N:7]=1)=[O:5])[CH3:2].[CH:27]([NH2:30])([CH3:29])[CH3:28].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH2:11][NH:30][CH:27]([CH3:29])[CH3:28])=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[N:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 11430Potassium CarbonateHCID 587609464-Bromomethyl-1-(2-chloro-phenyl)-5-(4-chloro-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 587609561-(2-Chloro-phenyl)-5-(4-chloro-phenyl)-4-(isopropylamino-methyl)-1H-pyrazole-3-carboxylic acid ethyl esterYield 21%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-bromomethyl-1-(2-chloro-phenyl)-5-(4-chloro-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester I-4b (200 mg, 0.44 mmol), isopropyl amine (26 mg, 0.44 mmol), K2CO3 (182 mg, 1.32 mmol) in CH3CN (5 ml) was stirred for 17 hours at room temperature. The reaction mixture was filtered to remove insoluble material and concentrated under vacuum. The residue was diluted with EtOAc and the organic solution was washed with H2O and sat'd aq. NaCl, dried, and concentrated in vacua. The crude residue was purified on SiO2-gel chromatography using a solvent gradient of 20% EtOAc/hexanes to 75% EtOAc/hexanes to give the product (I-4c) as an amorphous solid (40 mg, 21%): +APCI MS (M+1) 432.2.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove insoluble material
  3. concentrationconcentrated under vacuum
  4. additionThe residue was diluted with EtOAc
  5. washthe organic solution was washed with H2O
  6. customdried
  7. concentrationconcentrated in vacua
  8. customThe crude residue was purified on SiO2-gel chromatography

Sources & evidence

ORD record
ord-9094a316da844d5db8afce536e7499b1
Source dataset
uspto-grants-2007_07
Patent number
US07241788B2

Reaction notes

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