1,2-Dichloroethane → 1-(t-Butoxycarbonyl)-4-(2-(2-pyridinyl)hydrazino)carbonyl-piperidine

HRID 1068226Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1068226
Cl.Cl.[NH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)[NH2:4].[C:11]([N:18]1[CH2:23][CH2:22][CH:21]([C:24](O)=[O:25])[CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl>[C:14]([O:13][C:11]([N:18]1[CH2:23][CH2:22][CH:21]([C:24]([NH:4][NH:3][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=2)=[O:25])[CH2:20][CH2:19]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 64543982-Pyridone hydrazone dihydrochloride

Produkt 1

HCID 211930971-(t-Butoxycarbonyl)-4-(2-(2-pyridinyl)hydrazino)carbonyl-piperidineAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 2-hydrazinopyridine dihydrochloride (2.49 g, 13.7 mmol) and 1-Boc-piperidine-4-carboxylic acid (3.14 g, 13.7 mmol) in 30 mL of CH2Cl2 was added DIPEA (5.96 mL) followed by HOBT (2.22 g, 16.4 mmol) and EDC (3.93 g, 20.5 mmol) at rt. After stirring at rt for 18 h, the reaction mixture was partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2 (3×). Combined organic phase was washed with brine and dried over anhydrous MgSO4. Concentration under reduced pressure afforded the title compound (3.3 g) as a white solid. 1H NMR (500 MHz, CDCl3): δ 1.47 (s, 9H), 1.68-1.76 (m, 2H), 1.86-1.88 (m, 2H), 2.44 (m, 1H), 2.70-2.90 (br, 2H), 4.15-4.22 (br, 2H), 6.71 (d, J=8.5 Hz, 1H), 6.81 (t, J=6.4 Hz, 1H), 7.56 (m, 1H), 8.11 (d, J=5.0 Hz, 1H), 8.20˜8.55 (br s, 1H).

Aufarbeitung

  1. customthe reaction mixture was partitioned between CH2Cl2 and water
  2. extractionThe aqueous layer was extracted with CH2Cl2 (3×)
  3. washCombined organic phase was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationConcentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-284b0860f21640eb8a2aada83e60948d
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248755B1

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