Triethylamine → N-(3-chloro-4-(4-isobutyrylpiperazin-1-yl)phenyl)picolinamide

HRID 38249

Reaction equation

HRID 38249 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](Cl)=[O:9].CCN(CC)CC.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][N:28]([C:31](=[O:35])[CH:32]([CH3:34])[CH3:33])[CH2:27][CH2:26]2)=[C:21]([Cl:36])[CH:20]=1>C(Cl)Cl>[Cl:36][C:21]1[CH:20]=[C:19]([NH:18][C:8](=[O:9])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=2)[CH:24]=[CH:23][C:22]=1[N:25]1[CH2:30][CH2:29][N:28]([C:31](=[O:35])[CH:32]([CH3:33])[CH3:34])[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 135033Picolinoyl Chloride HydrochlorideHCID 9369261-(4-(4-Amino-2-chlorophenyl)piperazin-1-yl)-2-methylpropan-1-one

Product 1

HCID 42645025N-(3-chloro-4-(4-isobutyrylpiperazin-1-yl)phenyl)picolinamideYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to Scheme 4 Step 3: Picolinoyl chloride hydrochloride (0.93 mmol, 178 mg) and Et3N (1.86 mmol, 0.26 mL) were added to a solution of 1-(4-(4-amino-2-chlorophenyl)piperazin-1-yl)-2-methylpropan-1-one (0.62 mmol, 175 mg) in DCM (3 mL) at 0° C. The reaction mixture was stirred at room temperature for 2 hours. The organic phase was washed with a saturated solution of NaHCO3. The aqueous phase was extracted with AcOEt. The organic phase was washed with brine, was dried over Na2SO4, was filtered and was concentrated under reduced pressure. The crude product was purified by flash chromatography over C18 column using water/ACN (60:40) as eluent to afford N-(3-chloro-4-(4-isobutyrylpiperazin-1-yl)phenyl)picolinamide (0.11 mmol, 42 mg, 18%) as a white solid.

Workup

  1. washThe organic phase was washed with a saturated solution of NaHCO3
  2. extractionThe aqueous phase was extracted with AcOEt
  3. washThe organic phase was washed with brine
  4. dry with materialwas dried over Na2SO4
  5. filtrationwas filtered
  6. concentrationwas concentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography over C18 column

Sources & evidence

ORD record
ord-bf9a8f47cc0d45d592b8c2e6d4a9879b
Source dataset
uspto-grants-2013_09
Patent number
US08524726B2

Linked notes

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