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 1095375Notes

Reaction equation

HRID 1095375 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 57446245tert-butyl 4-[(4-oxo-2-phenyl-4,5-dihydro-2H-pyrazolo[3,4-c]quinolin-1-yl)acetyl]piperazine-1-carboxylateYield 85.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-6028b2dbf5014a05a72999156076e94c
Source dataset
uspto-grants-2012_03
Patent number
US08138173B2

Reaction notes

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