Ethanolamine → 1-[N-(2-Hydroxyethyl)carbamoyl]-4-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzene

HRID 582296Notes

Reaction equation

HRID 582296 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]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][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(Cl)(=O)C(C)(C)C.[NH2:42][CH2:43][CH2:44][OH:45]>C(Cl)Cl>[OH:45][CH2:44][CH2:43][NH:42][C:23]([C:22]1[CH:26]=[CH:27][C:19]([C:17]([N:14]2[CH2:15][CH2:16][N:11]([C:6]3[C:5]([NH:4][CH:1]([CH3:2])[CH3:3])=[CH:10][CH:9]=[CH:8][N:7]=3)[CH2:12][CH2:13]2)=[O:18])=[CH:20][CH:21]=1)=[O:24]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 8471Triethylamine2×HCID 62493Pivaloyl chlorideHCID 109595584-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoic acid

Product 1

HCID 110801221-[N-(2-Hydroxyethyl)carbamoyl]-4-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzeneYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

4-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoic acid (1.5 g) was dissolved in methylene chloride (50 ml) and then, triethylamine (0.7 ml) was added and cooled. Pivaloyl chloride(0.58 ml) was added slowly to the solution at 0~5° C. and the mixture was stirred at 5° C. for 2 hours. And then, triethylamine (0.7 ml) and 2-aminoethanol(1.27 g) were added in order, the solution was stirred at 0~5° C. for 2 hours and heated slowly to 20~25° C. and stirred for 30 minutes. The reaction mixture was washed with water twice and the solvent was concentrated under reduced pressure. The concentrated residue was crystallized by treatment with ether and further recrystallized using isopropanol and ether. The recrystallized product was filtered and dried to give 1.34 g (yield: 80%) of the desired compound as a white powder.

Workup

  1. temperaturecooled
  2. stirringthe solution was stirred at 0~5° C. for 2 hours
  3. temperatureheated slowly to 20~25° C.
  4. stirringstirred for 30 minutes
  5. washThe reaction mixture was washed with water twice
  6. concentrationthe solvent was concentrated under reduced pressure
  7. customThe concentrated residue was crystallized by treatment with ether
  8. customfurther recrystallized
  9. filtrationThe recrystallized product was filtered
  10. customdried

Sources & evidence

ORD record
ord-7fb65c950ed74fbeada699147c6f1b65
Source dataset
uspto-grants-1999_07
Patent number
US05922871

Reaction notes

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