N,N-Dimethyl-1,3-propanediamine → HCID 178483540, compound

HRID 1793398Notes

Reaction equation

HRID 1793398 reaction equation
[CH:1]1([C:4]2[NH:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:12]3[C:13]=2[C:14](=[O:26])[N:15]([C:17]2[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=2)[N:16]=3)[CH2:3][CH2:2]1.[CH3:27][N:28]([CH3:33])[CH2:29][CH2:30][CH2:31][NH2:32]>O1CCCC1>[CH3:27][N:28]([CH3:33])[CH2:29][CH2:30][CH2:31][NH:32][C:21](=[O:22])[C:20]1[CH:19]=[CH:18][C:17]([N:15]2[C:14](=[O:26])[C:13]3=[C:4]([CH:1]4[CH2:3][CH2:2]4)[NH:5][C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=4[C:12]3=[N:16]2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 178521111HCID 178521111, compound

Product 1

HCID 178483540HCID 178483540, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a partial solution of 4-(4-cyclopropyl-3-oxo-3,5-dihydro-pyrazolo[4,3-c]quinolin-2-yl)-benzoyl chloride (0.1 g, 0.28 mmol) in tetrahydrofurane (6 ml) under nitrogen was added a solution of 3-dimethylamino-propyl amine (0.03 g, 0.3 mmol) in tetrahydrofurane (3 ml). The mixture was stirred at RT for 3 h. The solvent was removed under reduced pressure and the yellow solid was washed with a little saturated sodium bicarbonate, water and dried under vacuo to yield N-(3-Dimethylamino propyl)-4-(4-cyclopropyl-3-oxo-3,5-dihydro-pyrazolo[4,3-c]quinolin-2-yl]-benzamide (57 mg, 47%) as a yellow solid. LCMS m/z 430.11 [M+H]+ @ RT 0.99 min: 100% purity.

Workup

  1. customThe solvent was removed under reduced pressure
  2. washthe yellow solid was washed with a little saturated sodium bicarbonate, water
  3. customdried under vacuo

Sources & evidence

ORD record
ord-e5ce23572c0a4884939891bce2bc781d
Source dataset
uspto-grants-2006_07
Patent number
US07081456B2

Reaction notes

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