8-Quinolinecarboxylic acid → 1-tert-butoxycarbonyl-2(S)-(2-hydroxyethyl)-4-(8-quinolinylcarbonyl)piperazine

HRID 1598462Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1598462
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([OH:13])=O)[CH:4]=[CH:3][CH:2]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[C:36]([O:40][C:41]([N:43]1[CH2:48][CH2:47][NH:46][CH2:45][C@@H:44]1[CH2:49][CH2:50][OH:51])=[O:42])([CH3:39])([CH3:38])[CH3:37]>CN(C=O)C.C(N(CC)CC)C>[C:36]([O:40][C:41]([N:43]1[CH2:48][CH2:47][N:46]([C:11]([C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[N:1]=[CH:2][CH:3]=[CH:4]3)=[O:13])[CH2:45][C@@H:44]1[CH2:49][CH2:50][OH:51])=[O:42])([CH3:39])([CH3:38])[CH3:37]

Komponenten

7

Edukt 4

HCID 665828-Quinolinecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12046236(S)-tert-butyl 2-(2-hydroxyethyl)piperazine-1-carboxylate

Produkt 1

HCID 228841311-tert-butoxycarbonyl-2(S)-(2-hydroxyethyl)-4-(8-quinolinylcarbonyl)piperazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

8-Quinoline carboxylic acid (1.00 g, 5.78 mmol), EDC.HCl (1.22 g, 6.38 mmol), HOBT (1.77 g, 13.1 mmol) in DMF at pH 7 (adjusted with triethylamine) was stirred at 20° C. for 15 min. 1-tert-Butoxycarbonyl-2(S)-(2-hydroxyethyl)piperazine (1.33 g, 6.71 mmol) was added and the reaction stirred overnight. DMF was removed in vacuo, and the residue taken up in 1:1:1 THF, methanol, and 5% aqueous sodium hydroxide. This was stirred at 20° C. for 72 h. The volatiles were removed in vacuo, and the residue partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic phase was washed with saturated sodium chloride solution, then dried over magnesium sulfate. The title compound was obtained as a foam (1.2 g).

Aufarbeitung

  1. customDMF was removed in vacuo
  2. stirringThis was stirred at 20° C. for 72 h
  3. customThe volatiles were removed in vacuo
  4. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate solution
  5. washThe organic phase was washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-2b58dd87d65349509c6a2f376bbbd2e7
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05736539

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