Potassium Carbonate → HCID 67052460, compound

HRID 1907965Notes

Reaction equation

HRID 1907965 reaction equation
Cl.[Cl:2][CH2:3][C:4]([NH:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([C:16]=1[NH:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[N:14][CH:13]=[CH:12][CH:11]=2)=O.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[Cl:2][CH2:3][C:4]1[N:17]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:16]2[C:15]3[N:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:6]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67052355HCID 67052355, compound

Product 1

HCID 67052460HCID 67052460, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To a solution of 2-chloro-N-{4-[(2-methylpropyl)amino][1,5]naphthyridin-3-yl}acetamide hydrochloride (from Part C, approximately 70 mmol) in 3:1 ethanol/water (280 mL) was added 6 M aqueous potassium carbonate (17.5 mL). The reaction mixture was stirred at room temperature over the weekend. The volatiles were removed under reduced pressure and the residue was partitioned between dichloromethane (200 mL) and brine (100 mL). The aqueous layer was extracted with dichloromethane (2×50 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 19.5 g of 2-(chloromethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridine, which contained a small amount of dichloromethane and was used without further purification in the next step.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue was partitioned between dichloromethane (200 mL) and brine (100 mL)
  3. extractionThe aqueous layer was extracted with dichloromethane (2×50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-034313fe20b343cc9a253e6e9f4133ae
Source dataset
uspto-grants-2013_12
Patent number
US08598192B2

Reaction notes

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