Triethylamine → HCID 57255835, compound

HRID 582303Notes

Reaction equation

HRID 582303 reaction equation
[CH:1]([NH:4][C:5]1[C:6]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([C:19]3[CH:27]=CC(C(O)=O)=C[CH:20]=3)=[O:18])[CH2:13][CH2:12]2)=[N:7][CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.[C:35](Cl)(=[O:40])[C:36](C)([CH3:38])[CH3:37].[CH3:42][N:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1>C(Cl)Cl>[CH:1]([NH:4][C:5]1[C:6]([N:11]2[CH2:12][CH2:13][N:14]([C:17]([C:19]3[CH:20]=[CH:38][C:36]([C:35]([N:46]4[CH2:47][CH2:48][N:43]([CH3:42])[CH2:44][CH2:45]4)=[O:40])=[CH:37][CH:27]=3)=[O:18])[CH2:15][CH2:16]2)=[N:7][CH:8]=[CH:9][CH:10]=1)([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 531671-MethylpiperazineHCID 62493Pivaloyl chlorideHCID 109595584-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoic acid

Product 1

HCID 57255835HCID 57255835, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

4-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoic acid (1.2 g) was dissolved in methylene chloride (40 ml) and then, triethylamine (0.6 ml) was added and cooled. Pivaloyl chloride (0.46 ml) was added slowly to the solution at 0~5° C. and the mixture was stirred at 5° C. for 2 hours. With the addition of triethylamine (0.6 ml) and 1-methylpiperazine (0.38 g), the reaction mixture was stirred at 5° C. for 2 hours and heated slowly to 20° C. and stirred for 30 minutes. The reaction mixture was washed with water and aqueous sodium bicarbonate and the solvent was concentrated under reduced pressure. The concentrated residue was crystallized by treatment with hexane and ether, and further recrystallized using ethyl acetate and isopropyl ether. The recrystallized product was filtered and dried to give 1.15 g (yield: 78%) of the desired compound as white powder.

Workup

  1. temperaturecooled
  2. stirringthe reaction mixture was stirred at 5° C. for 2 hours
  3. temperatureheated slowly to 20° C.
  4. stirringstirred for 30 minutes
  5. washThe reaction mixture was washed with water and aqueous sodium bicarbonate
  6. concentrationthe solvent was concentrated under reduced pressure
  7. customThe concentrated residue was crystallized by treatment with hexane and ether
  8. customfurther recrystallized
  9. filtrationThe recrystallized product was filtered
  10. customdried

Sources & evidence

ORD record
ord-81c3b0c03cfd4c2f900e89065e41145f
Source dataset
uspto-grants-1999_07
Patent number
US05922871

Reaction notes

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