Sodium Hydroxide → 1-(4-Chlorophenyl)-N-(3-cyano-4-[4-(N-(2-hydroxyethyl)amino)piperidin-1-yl]phenyl}-5-methylpyrazole-4-carboxamide

HRID 1744624Notes

Reaction equation

HRID 1744624 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14](Cl)=[O:15])[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[NH2:17][C:18]1[CH:19]=[CH:20][C:21]([N:26]2[CH2:31][CH2:30][CH:29]([N:32](C(OC(C)(C)C)=O)[CH2:33][CH2:34][OH:35])[CH2:28][CH2:27]2)=[C:22]([CH:25]=1)[C:23]#[N:24].[OH-].[Na+]>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([NH:17][C:18]3[CH:19]=[CH:20][C:21]([N:26]4[CH2:31][CH2:30][CH:29]([NH:32][CH2:33][CH2:34][OH:35])[CH2:28][CH2:27]4)=[C:22]([C:23]#[N:24])[CH:25]=3)=[O:15])[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27761281-(4-chlorophenyl)-5-methyl-1H-pyrazole-4-carbonyl chlorideHCID 222280265-amino-2-[4-(N-tert-butoxycarbonyl-2-hydroxyethylamino)piperidin-1-yl]benzonitrile

Product 1

HCID 222280481-(4-Chlorophenyl)-N-(3-cyano-4-[4-(N-(2-hydroxyethyl)amino)piperidin-1-yl]phenyl}-5-methylpyrazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The reaction and treatment in the same manner as in Example 150 were conducted using 1-(4-chlorophenyl)-5-methylpyrazole-4-carboxylic chloride (1.19 g) and 5-amino-2-[4-(N-tert-butoxycarbonyl-N-(2-hydroxyethyl)amino)piperidin-1-yl]benzonitrile and the resulting mixture was further stirred in trifluoroacetic acid (10 ml) under ice-cooling for 1 h. The reaction mixture was treated with aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was recrystallized from ethanol to give the title compound (0.29 g), melting point: 181° C.

Workup

  1. customThe reaction and treatment in the same manner as in Example 150
  2. temperaturecooling for 1 h
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-cfbdde389f0642e0ab02cd9c38f9b2df
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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