N,N-Dimethyl-1,3-propanediamine → HCID 178483542, compound

HRID 1591648Notes

Reaction equation

HRID 1591648 reaction equation
[F:1][C:2]1[C:11]2[NH:10][CH:9]=[C:8]3[C:12](=[O:24])[N:13]([C:15]4[CH:23]=[CH:22][C:18]([C:19]([Cl:21])=[O:20])=[CH:17][CH:16]=4)[N:14]=[C:7]3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:25][N:26]([CH3:31])[CH2:27][CH2:28][CH2:29][NH2:30]>O1CCCC1>[ClH:21].[CH3:25][N:26]([CH3:31])[CH2:27][CH2:28][CH2:29][NH:30][C:19](=[O:20])[C:18]1[CH:22]=[CH:23][C:15]([N:13]2[C:12](=[O:24])[C:8]3=[CH:9][NH:10][C:11]4[C:2]([F:1])=[CH:3][CH:4]=[CH:5][C:6]=4[C:7]3=[N:14]2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 178521112HCID 178521112, compound

Product 1

HCID 178483542HCID 178483542, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a partial solution of 4-(6-Fluoro-3-oxo-3,5-dihydro-pyrazolo[4,3-c]quinolin-2-yl]-benzoyl chloride (0.1 g, 0.3 mmol) in tetrahydrofurane (5 ml) under nitrogen was added a solution of 3-dimethylamino-propyl amine (0.03 g, 0.3 mmol) in tetrahydrofurane. The mixture was stirred at rt for 90 minutes. The solvent was removed under reduced pressure and the yellow solid was purified via FCC silica gel (gradient elution, MeOH:H2O, Fluka C18 reverse phase) to yield N-(3-Dimethylamino propyl)-4-(6-fluoro-3-oxo-3,5-dihydro-pyrazolo[4,3-c]quinolin-2-yl]-benzamide hydrochloride (70 mg, 53%) as a yellow solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe yellow solid was purified via FCC silica gel (gradient elution, MeOH:H2O, Fluka C18 reverse phase)

Sources & evidence

ORD record
ord-2850193df1264cfabf5b3341721c75e3
Source dataset
uspto-grants-2007_11
Patent number
US07291612B2

Reaction notes

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