1-Hydroxybenzotriazole → tert-butyl 4-[(4-oxo-2-phenyl-4,5-dihydro-2H-pyrazolo[3,4-c]quinolin-1-yl)acetyl]piperazine-1-carboxylate

HRID 1095375Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1095375
[O:1]=[C:2]1[C:11]2=[N:12][N:13]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:14]([CH2:15][C:16](O)=[O:17])=[C:10]2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[NH:3]1.[C:25]([N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C=O)C>[O:1]=[C:2]1[C:11]2=[N:12][N:13]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:14]([CH2:15][C:16]([N:35]3[CH2:34][CH2:33][N:32]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:37][CH2:36]3)=[O:17])=[C:10]2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[NH:3]1

Komponenten

6

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57446227HCID 57446227, Verbindung

Produkt 1

HCID 57446245tert-butyl 4-[(4-oxo-2-phenyl-4,5-dihydro-2H-pyrazolo[3,4-c]quinolin-1-yl)acetyl]piperazine-1-carboxylateAusbeute 85,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of (4-oxo-2-phenyl-4,5-dihydro-2H-pyrazolo[3,4-c]quinolin-1-yl)acetic acid (1.50 g, 4.70 mmol), N-Boc piperazine (0.96 g, 5.17 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.35 g, 7.05 mmol), 1-hydroxybenzotriazole (0.95 g, 7.05 mmol) and 20 mL of DMF was stirred at ambient temperature overnight. The mixture was concentrated under reduced pressure. The residue was triturated with acetonitrile, isolated by filtration, and dried to afford 1.96 g of tert-butyl 4-[(4-oxo-2-phenyl-4,5-dihydro-2H-pyrazolo[3,4-c]quinolin-1-yl)acetyl]piperazine-1-carboxylate as a pale yellow solid.

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe residue was triturated with acetonitrile
  3. customisolated by filtration
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6028b2dbf5014a05a72999156076e94c
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138173B2

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