3-Aminopyridine → HCID 46238383, compound

HRID 2170902Notes

Reaction equation

HRID 2170902 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[O:13][CH:14]=[CH:15][CH:16]=1)[CH:6]=[C:5]2[C:17]([OH:19])=O.CCN=C=NCCCN(C)C.Cl.[CH:32]1[CH:33]=C[C:35]2[N:40](O)N=[N:38][C:36]=2[CH:37]=1.NC1C=NC=CC=1>CN(C=O)C.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[O:13][CH:14]=[CH:15][CH:16]=1)[CH:6]=[C:5]2[C:17]([NH:38][C:36]1[CH:35]=[N:40][CH:33]=[CH:32][CH:37]=1)=[O:19]

Participants

8

Reactant 4

HCID 100093-AminopyridineHCID 757711-HydroxybenzotriazoleHCID 6861526-Bromo-2-(2-furanyl)-4-quinolinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 46238383HCID 46238383, compoundYield 32.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 250 ml three necked round bottom flask equipped with thermo pocket under argon atmosphere was added 6-bromo-2-(furan-2-yl)quinoline-4-carboxylic acid (5 g) in DMF (15 ml). The solution was stirred for 5 minutes. After 5 minutes, EDAC.HCl (N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride) (3.6 g), HOBT (2.54 g) and DMAP (3.83 g) were added at RT and the reaction mixture was stirred at room temperature for 0.5 h. 3-amino pyridine (1.6 g) was then added in one lot and the reaction was allowed to stir at RT for 12 hours. The completion of the reaction was monitored by TLC using ethyl acetate:hexanes (5:5) as a mobile phase. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (100 ml) and then washed with water (5×100 ml). The ethyl acetate layer was dried over anhydrous sodium sulphate and then solvent was distilled out and the crude was subjected to purification by silica gel column chromatography, eluting with 1.5% methanol in methylene chloride to provide 6-bromo-2-(furan-2-yl)-N-(pyridin-3-yl)quinoline-4-carboxamide (2.0 g).

Workup

  1. waitAfter 5 minutes
  2. stirringthe reaction mixture was stirred at room temperature for 0.5 h
  3. stirringto stir at RT for 12 hours
  4. customAfter completion of the reaction
  5. washwashed with water (5×100 ml)
  6. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulphate
  7. distillationsolvent was distilled out
  8. customthe crude was subjected to purification by silica gel column chromatography
  9. washeluting with 1.5% methanol in methylene chloride

Sources & evidence

ORD record
ord-089fbad7a11d4526b1a75dd96bde2d6f
Source dataset
uspto-grants-2015_06
Patent number
US09051305B2

Reaction notes

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