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

HRID 1793400Notes

Reaction equation

HRID 1793400 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-d0a9987fba804406a5ad7e3620f944c8
Source dataset
uspto-grants-2006_07
Patent number
US07081456B2

Reaction notes

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