Nicotinic Acid → HCID 18467083, compound

HRID 2229407Notes

Reaction equation

HRID 2229407 reaction equation
[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[C:7]([NH:23][C:24]([NH:26][C:27]2[C:32]([CH:33]([CH3:35])[CH3:34])=[CH:31][CH:30]=[C:29]([NH2:36])[C:28]=2[CH:37]([CH3:39])[CH3:38])=[O:25])[C:6]1=[O:40])[CH2:2][CH2:3][CH3:4].[C:41](O)(=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[N:44][CH:43]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.CCN(CC)CC>CN(C=O)C.O>[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][N:13]=2)[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[C:7]([NH:23][C:24]([NH:26][C:27]2[C:32]([CH:33]([CH3:35])[CH3:34])=[CH:31][CH:30]=[C:29]([NH:36][C:41]([C:42]3[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=3)=[O:48])[C:28]=2[CH:37]([CH3:39])[CH3:38])=[O:25])[C:6]1=[O:40])[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 5

HCID 938Nicotinic AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18467149HCID 18467149, compound

Product 1

HCID 18467083HCID 18467083, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of N-[1-butyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N′-(2,6-diisopropyl-3-aminophenyl)urea (300 mg, 0.485 mmol), nicotinic acid (66 mg, 0.533 mmol), 1-hydroxybenzotriazole (131 mg, 0.97 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (93 mg, 0.485 mmol) and Et3N (0.06 ml, 0.485 mmol) in DMF (10 ml) is stirred at room temperature overnight. To the reaction solution is added water, and the mixture is extracted with ethyl acetate. The organic layer is washed twice with an aqueous ammonium chloride solution, and washed twice with an aqueous sodium hydrogen carbonate solution. The solvent is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography to give the title compound (243 mg, 0.373 mmol) as white crystals.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe organic layer is washed twice with an aqueous ammonium chloride solution
  3. washwashed twice with an aqueous sodium hydrogen carbonate solution
  4. concentrationThe solvent is concentrated under reduced pressure
  5. customthe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f983f1bc9a894fb3be642350b152cc62
Source dataset
uspto-grants-2002_07
Patent number
US06420381B1

Reaction notes

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