Hydrochloric Acid → HCID 18467098, compound

HRID 2229405Notes

Reaction equation

HRID 2229405 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][C:30]([NH:36][CH2:37][C:38]3[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=3)=[CH:29][C:28]=2[CH:44]([CH3:46])[CH3:45])=[O:25])[C:6]1=[O:47])[CH2:2][CH2:3][CH3:4].C=O.Cl.[C:51]([BH3-])#N.[Na+]>CO.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]([CH3:34])[CH3:35])=[CH:31][C:30]([N:36]([CH2:37][C:38]3[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=3)[CH3:51])=[CH:29][C:28]=2[CH:44]([CH3:46])[CH3:45])=[O:25])[C:6]1=[O:47])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 18467088HCID 18467088, compound

Product 1

HCID 18467098HCID 18467098, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of N-[1-butyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N′-[2,6-diisopropyl-4-(3-pyridylmethylamino)-phenyl]urea (476 mg, 0.752 mmol) in methanol (5 ml) are added a 37% aqueous formaldehyde solution (122 mg, 1.50 ml) and conc. hydrochloric acid (0.13 ml, 1.50 ml) at room temperature. The mixture is cooled with ice, and the thereto is added sodium cyanoborohydride (71.0 mg, 1.13 ml), and the mixture is stirred at room temperature for 5 hours. To the mixture is added water, and the mixture is extracted with ethyl acetate. The organic layer is extracted twice with sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate. The solvent is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography to give the title compound (445 mg, 0.684 mmol) as colorless amorphous.

Workup

  1. temperatureThe mixture is cooled with ice
  2. extractionthe mixture is extracted with ethyl acetate
  3. extractionThe organic layer is extracted twice with sodium hydrogen carbonate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe solvent is concentrated under reduced pressure
  6. customthe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dc250d2abb9b441cb0771a8f092514b4
Source dataset
uspto-grants-2002_07
Patent number
US06420381B1

Reaction notes

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