Triethylamine → HCID 54288884, compound

HRID 582309Notes

Reaction equation

HRID 582309 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]([OH:25])=O)=[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][C:43]([CH3:47])([CH3:46])[CH2:44][OH:45]>C(Cl)Cl.N1C=CC=CC=1>[CH3:46][C:43]([NH:42][C:23]([C:22]1[CH:21]=[CH:20][C:19]([C:17]([N:14]2[CH2:15][CH2:16][N:11]([C:6]3[C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[CH:10][CH:9]=[CH:8][N:7]=3)[CH2:12][CH2:13]2)=[O:18])=[CH:27][CH:26]=1)=[O:25])([CH3:47])[CH2:44][OH:45]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 118072-Amino-2-methyl-1-propanolHCID 62493Pivaloyl chlorideHCID 109595584-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoic acid

Product 1

HCID 54288884HCID 54288884, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 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 (45 ml), and then triethylamine (0.73 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, pyridine (0.65 ml) and 2-amino-2-methyl-1-propanol (0.4 g) were added in order, the solution was stirred at 0~5° C. for 2 hours and heated to 20° C. and stirred for 1 hour. The reaction mixture was washed with water twice and dried over anhydrous magnesium sulfate. Then, the solvent was concentrated under reduced pressure. The concentrated residue was crystallized by treatment with ether and further recrystallized using ethyl acetate and ether. The recrystallized product was filtered and dried to give 1.5 g (yield: 84%) of a desired compound.

Workup

  1. temperaturecooled
  2. stirringthe solution was stirred at 0~5° C. for 2 hours
  3. temperatureheated to 20° C.
  4. stirringstirred for 1 hour
  5. washThe reaction mixture was washed with water twice
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThen, the solvent was concentrated under reduced pressure
  8. customThe concentrated residue was crystallized by treatment with ether
  9. customfurther recrystallized
  10. filtrationThe recrystallized product was filtered
  11. customdried

Sources & evidence

ORD record
ord-d6abe4ced3bc46419728c40ed0ba386d
Source dataset
uspto-grants-1999_07
Patent number
US05922871

Reaction notes

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