Triethylamine → HCID 22716712, compound

HRID 1582986Notes

Reaction equation

HRID 1582986 reaction equation
O1CCOCC1.[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2[C:23]3[C:18](=[N:19][C:20]([CH3:24])=[CH:21][CH:22]=3)[N:17]([CH2:25][CH3:26])[C:16](=[O:27])[C:15]=2[C:28]2[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=2)C(O)=O)[CH:11]=[CH:12][CH:13]=1.C1C=CC(P([N:51]=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.C(N(CC)CC)C>C(OCC)(=O)C.C(O)(C)(C)C>[ClH:7].[NH2:51][C:30]1[CH:29]=[C:28]([C:15]2[C:16](=[O:27])[N:17]([CH2:25][CH3:26])[C:18]3[C:23]([C:14]=2[C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([Cl:7])[CH:9]=2)=[CH:22][CH:21]=[C:20]([CH3:24])[N:19]=3)[CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 199401P,P-Diphenylphosphinic azideHCID 12991199HCID 12991199, compound

Product 1

HCID 22716712HCID 22716712, compound

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 20 ml dioxane solution containing 783 mg of 3-[4-(3-chlorophenyl)-1-ethyl-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]benzoic acid were added 0.48 ml of DPPA, 0.31 ml of triethylamine and 0.89 ml of t-butanol, followed by heating under reflux for 18 hours. After cooling to room temperature and concentration of the reaction mixture under a reduced pressure, ethyl acetate was added to the resulting residue, followed by washing with saturate sodium bicarbonate aqueous solution and saturated brine. The organic layer was concentrated under a reduced pressure and the resulting residue was purified by a silica gel column chromatography (hexane-ethyl acetate). To 680 mg portion of 680 mg of thus obtained compound in 5 ml of ethyl acetate was added 5 ml of a 4M hydrogen chloride-ethyl acetate solution under ice cooling, followed by stirring at room temperature for 2 hours. The reaction mixture was concentrated and the resulting crude crystals were recrystallized from ethanol-ethyl acetate to obtain 486 mg of 3-(3-aminophenyl)-4-(3-chlorophenyl)-1-ethyl-7-methyl-1,8-naphthyridin-2(1H)-one monohydrochloride as pale brown crystals.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 18 hours
  3. washby washing with saturate sodium bicarbonate aqueous solution and saturated brine
  4. concentrationThe organic layer was concentrated under a reduced pressure
  5. customthe resulting residue was purified by a silica gel column chromatography (hexane-ethyl acetate)
  6. additionTo 680 mg portion of 680 mg of thus obtained compound in 5 ml of ethyl acetate was added 5 ml of a 4M hydrogen chloride-ethyl acetate solution under ice cooling
  7. concentrationThe reaction mixture was concentrated
  8. customthe resulting crude crystals were recrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-769eb87536fc4f1f82f66aeddf4b1fa2
Source dataset
uspto-grants-2004_05
Patent number
US06740662B1

Reaction notes

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