Sodium Chloride → N-(2-dimethylamino-ethyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxamide

HRID 1969994Notes

Reaction equation

HRID 1969994 reaction equation
ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.CN1CCOCC1.[CH3:30][N:31]([CH3:35])[CH2:32][CH2:33][NH2:34].[O:36]=[C:37]1[C:46]2[NH:47][CH:48]=[C:49]([C:50](O)=[O:51])[C:45]=2[C:44]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[NH:38]1.[Cl-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:30][N:31]([CH3:35])[CH2:32][CH2:33][NH:34][C:50]([C:49]1[C:45]2[C:44]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[NH:38][C:37](=[O:36])[C:46]=2[NH:47][CH:48]=1)=[O:51]

Participants

9

Reactant 6

HCID 5234Sodium ChlorideHCID 79724-MethylmorpholineHCID 66053N,N-DimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 120650844-oxo-3H,4H,5H-pyrrolo[2,3-c]quinoline-1-carboxylic acid

Product 1

HCID 15605162N-(2-dimethylamino-ethyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxamideYield 13.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

49 mg (0.36 mmol) of 1-hydroxybenzotriazole, 69 mg (0.36 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 73 μL (0.66 mmol) of N-methylmorpholine and 40 μL (0.36 mmol) of N,N-dimethylethylenediamine are added to 75 mg (0.33 mmol) of 4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid (synthesis 75) suspended in 0.7 ml of anhydrous dimethylformamide. The reaction mixture is stirred overnight at room temperature. The mixture is diluted with ethyl acetate (20 mL) and a saturated solution of sodium chloride (20 mL). The two phases are separated and the aqueous phase is extracted with ethyl acetate (3×20 mL). The organic phases are combined, washed with n aqueous solution of potassium carbonate (10%) (3×40 mL), water (40 mL) and a saturated solution of sodium chloride (50 mL), dried over magnesium sulfate and evaporated. The residue obtained is triturated in diethyl ether to give 13 mg (13%) of N-(2-dimethylamino-ethyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-carboxamide in the form of a light brown solid.

Workup

  1. customThe two phases are separated
  2. extractionthe aqueous phase is extracted with ethyl acetate (3×20 mL)
  3. washwashed with n aqueous solution of potassium carbonate (10%) (3×40 mL), water (40 mL)
  4. dry with materiala saturated solution of sodium chloride (50 mL), dried over magnesium sulfate
  5. customevaporated
  6. customThe residue obtained
  7. customis triturated in diethyl ether

Sources & evidence

ORD record
ord-22c304326af9449cbad2b5402534a2bd
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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