Sodium Carbonate → HCID 25119520, compound

HRID 2382160Notes

Reaction equation

HRID 2382160 reaction equation
[CH2:1]([NH:3][C:4]([NH2:6])=[O:5])[CH3:2].[N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][N:15]=2)[CH:10]=[CH:9][CH:8]=1.[CH2:17]([CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:30](=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O>[CH2:17]([CH:24]1[CH2:29][CH2:28][N:27]([CH2:2][CH2:1][NH:3][C:4]([NH:6][C:14]2[CH:13]=[CH:12][C:11]3[C:10](=[CH:9][CH:8]=[N:7][C:16]=3[CH3:30])[N:15]=2)=[O:5])[CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 317384-BenzylpiperidineHCID 68596563HCID 68596563, compound

Product 1

HCID 25119520HCID 25119520, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of the ethylurea-naphthyridine intermediate (44 mg, 0.17 mmol) in 2 mL of DMF was added 4-benzylpiperidine (44 mg, 0.25 mmol) and sodium carbonate (0.141 g, 1.33 mmol). The reaction mixture was heated at 50° C. for 48 hours. The mixture was diluted with water (10 mL), extracted with two 10 mL portions of dichloromethane, and washed with brine (10 mL). The organic layer was dried over sodium sulfate, and purified by silica gel chromatography eluting with a gradient of dichloromethane/MeOH/NH4OH to yield 18 mg (27%) of desired. LCMS (EI) m/z 404 (M+1).

Workup

  1. extractionextracted with two 10 mL portions of dichloromethane
  2. washwashed with brine (10 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. custompurified by silica gel chromatography
  5. washeluting with a gradient of dichloromethane/MeOH/NH4OH
  6. customto yield 18 mg (27%)

Sources & evidence

ORD record
ord-15c72590b24a4bdb8b01333cc797dfdd
Source dataset
uspto-grants-2012_09
Patent number
US08258301B2

Reaction notes

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