Triethylamine → 1-[N-[(1S)-1-(Cyclohexylmethyl)-2-hydroxyethyl]carbamoyl]-4-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzene

HRID 582313Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 582313
[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.Cl.[NH2:43][C@@H:44]([CH2:47][CH:48]1[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]1)[CH2:45][OH:46]>C(Cl)Cl>[CH:48]1([CH2:47][C@H:44]([NH:43][C:23]([C:22]2[CH:26]=[CH:27][C:19]([C:17]([N:14]3[CH2:15][CH2:16][N:11]([C:6]4[C:5]([NH:4][CH:1]([CH3:2])[CH3:3])=[CH:10][CH:9]=[CH:8][N:7]=4)[CH2:12][CH2:13]3)=[O:18])=[CH:20][CH:21]=2)=[O:25])[CH2:45][OH:46])[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]1

Komponenten

6

Edukt 4

HCID 8471Triethylamine2×HCID 62493Pivaloyl chlorideHCID 109595584-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoic acidHCID 16212813(2S)-2-amino-3-cyclohexylpropan-1-ol hydrochloride

Produkt 1

HCID 573068291-[N-[(1S)-1-(Cyclohexylmethyl)-2-hydroxyethyl]carbamoyl]-4-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzeneAusbeute 100,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

4-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoic acid (1.5 g) was dissolved in methylene chloride (60 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 SoC for 2 hours. And then triethylamine (1.7 ml) and (S)-(+)-2-amino-3-cyclohexyl-1-propanol hydrochloride (0.87 g) were added in order, the solution was stirred at 0° C. for 3 hours and heated slowly to 20° C. and stirred for 1 hour. The reaction mixture was washed with water twice and the solvent was concentrated under reduced pressure. The concentrated residue was recrystallized using isopropanol and ether. The recrystallized product was filtered and dried to give 2.07 g (yield: 80%) of the desired compound. m.p.: 139~140° C.; 1H-NMR(CDCl3), ppm: δ 0.89~1.01(m, 2H), 1.22(m, 9H), 1.34(m, 1H), 1.45(m, 2H), 1.71(m, 4H), 1.81(m, 1H), 3.10(m, 4H), 3.51(m, 3H), 3.61(m, 1H), 3.76(m, 1H), 3.89(m, 2H), 4.13(m, 1H), 4.26(m, 1H), 6.59(m, 1H), 6.83(m, 1H), 6.95(m, 1H), 7.40(m, 2H), 7.67(m, 1H), 7.77(m, 2H)

Aufarbeitung

  1. temperaturecooled
  2. stirringthe solution was stirred at 0° C. for 3 hours
  3. stirringstirred for 1 hour
  4. washThe reaction mixture was washed with water twice
  5. concentrationthe solvent was concentrated under reduced pressure
  6. customThe concentrated residue was recrystallized
  7. filtrationThe recrystallized product was filtered
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f7822f3d360143459fdfac427544b875
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05922871

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