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

HRID 857475Notes

Reaction equation

HRID 857475 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 vacuo. 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 vacuo
  8. customThe crude residue was purified on SiO2-gel chromatography

Sources & evidence

ORD record
ord-0e4ea70c66644d9891b532287efed75a
Source dataset
uspto-grants-2006_12
Patent number
US07145012B2

Reaction notes

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