Water → 2-(1,4-Bis-(4-fluoro-phenyl)-1H-imidazol-2-yl)-1-(4-(4-methoxy-pyridin-2-yl)-piperazin-1-yl)-ethanone

HRID 1428949Notes

Reaction equation

HRID 1428949 reaction equation
C(O[C:4](=[O:25])[CH2:5][C:6]1[N:7]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[N:10]=1)C.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][N:31]=[C:30]([N:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[CH:29]=1.O>CN1C(=O)CCC1>[F:24][C:21]1[CH:22]=[CH:23][C:18]([N:7]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:10]=[C:6]2[CH2:5][C:4]([N:37]2[CH2:38][CH2:39][N:34]([C:30]3[CH:29]=[C:28]([O:27][CH3:26])[CH:33]=[CH:32][N:31]=3)[CH2:35][CH2:36]2)=[O:25])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 226481321-(4-Methoxypyridin-2-yl)piperazineHCID 86687938(1,4-bis-(4-fluoro-phenyl)-1H-imidazol-2-yl)-acetic acid ethyl ester

Product 1

HCID 715997712-(1,4-Bis-(4-fluoro-phenyl)-1H-imidazol-2-yl)-1-(4-(4-methoxy-pyridin-2-yl)-piperazin-1-yl)-ethanoneYield 31%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

70 mg (1,4-bis-(4-fluoro-phenyl)-1H-imidazol-2-yl)-acetic acid ethyl ester, 58 mg 1-(4-methoxy-pyridin-2-yl)-piperazine and 0.05 mLN,N-diisopropylethylamine in 2 mL NMP was stirred 50 min. at 180° C. under microwave condition. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried and evaporated. The residue was purified by HPLC (column: Waters Symmetry 50×140 mm 7 μm, mobile layer: water+0.3% HCOOH/methanol 10% until 90% in 14 min) to give 31 mg desired product.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was dried
  3. customevaporated
  4. customThe residue was purified by HPLC (column: Waters Symmetry 50×140 mm 7 μm, mobile layer: water+0.3% HCOOH/methanol 10% until 90% in 14 min)

Sources & evidence

ORD record
ord-95d582b243b644c2b3dc2b50f0572982
Source dataset
uspto-grants-2015_01
Patent number
US08937176B2

Reaction notes

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