Potassium Carbonate → N-{3-Cyano-4-[4-(2-hydroxyethyl)piperazin-1-yl]phenyl}-1-(4-fluorophenyl)pyrrole-2-carboxamide

HRID 1744592Notes

Reaction equation

HRID 1744592 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][CH:10]=[C:9]2[C:13]([OH:15])=O)=[CH:4][CH:3]=1.[NH2:16][C:17]1[CH:18]=[CH:19][C:20]([N:25]2[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][OH:33])[CH2:27][CH2:26]2)=[C:21]([CH:24]=1)[C:22]#[N:23].ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:22]([C:21]1[CH:24]=[C:17]([NH:16][C:13]([C:9]2[N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH:12]=[CH:11][CH:10]=2)=[O:15])[CH:18]=[CH:19][C:20]=1[N:25]1[CH2:26][CH2:27][N:28]([CH2:31][CH2:32][OH:33])[CH2:29][CH2:30]1)#[N:23]

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 173900441-(4-fluorophenyl)-1H-pyrrole-2-carboxylic acidHCID 176095935-Amino-2-[4-(2-hydroxyethyl)piperazin-1-yl]benzonitrile

Product 1

HCID 22228195N-{3-Cyano-4-[4-(2-hydroxyethyl)piperazin-1-yl]phenyl}-1-(4-fluorophenyl)pyrrole-2-carboxamideYield 35.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(4-Fluorophenyl)pyrrole-2-carboxylic acid (2 g), 5-amino-2-[4-(2-hydroxyethyl)piperazin-1-yl]benzonitrile (2.4 g), 1-hydroxybenzotriazole (1.8 g) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (2.2 g) were added to dimethylformamide (25 ml) and the mixture was stirred at room temperature for 5 h. The reaction mixture was treated with aqueous potassium carbonate solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (mobile phase:chloroform:methanol=100:1) to give an oily substance. The obtained oily substance was recrystallized from a mixed solvent of toluene-n-hexane to give the title compound (1.5 g), melting point: 170–171° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customafter which the solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (mobile phase:chloroform:methanol=100:1)
  6. customto give an oily substance
  7. customThe obtained oily substance was recrystallized from a mixed solvent of toluene-n-hexane

Sources & evidence

ORD record
ord-390c5e2179a641e698966627071479d8
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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