Potassium Carbonate → HCID 66958197, compound

HRID 1364047Notes

Reaction equation

HRID 1364047 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][CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[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][CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[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 66958132HCID 66958132, compound

Product 1

HCID 66958197HCID 66958197, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of tert-butyl 3-({3-[(chloroacetyl)amino][1,5]naphthyridin-4-yl}amino)propylcarbamate hydrochloride (from Part E, approximately 57.6 mmol) in 3:1 ethanol/water (240 mL) was added 6 M aqueous potassium carbonate. The reaction mixture was stirred at room temperature for 1 hour, 40° C. for 1.5 hour, then at room temperature overnight. The volatiles were removed under reduced pressure and the residue was partitioned between dichloromethane (250 mL) and water (150 mL). The aqueous layer was extracted with dichloromethane (2×75 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 18.9 g of tert-butyl 3-[2-(chloromethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]propylcarbamate.

Workup

  1. customat room temperature
  2. customovernight
  3. customThe volatiles were removed under reduced pressure
  4. customthe residue was partitioned between dichloromethane (250 mL) and water (150 mL)
  5. extractionThe aqueous layer was extracted with dichloromethane (2×75 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c454efb38b85449481e68f51bf5c7d9b
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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