Sodium Carbonate → HCID 58574225, compound

HRID 1619430Notes

Reaction equation

HRID 1619430 reaction equation
O=[C:2]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:10]([O:12]CC)=O.[NH2:15][C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][N:25]=1)[C:19]([O:21][CH3:22])=[O:20].C(=O)([O-])[O-].[Na+].[Na+]>ClCCCl>[CH3:22][O:21][C:19]([C:18]1[CH:23]=[CH:24][N:25]2[C:10](=[O:12])[C:3]3[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:2]=3[N:15]=[C:16]2[CH:17]=1)=[O:20]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 227421Ethyl 2-oxo-1-cyclooctanecarboxylateHCID 236984Methyl 2-aminopyridine-4-carboxylate

Product 1

HCID 58574225HCID 58574225, compoundYield 10.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of ethyl 2-oxocyclooctanecarboxylate (1 g, 5.05 mmol) and methyl 2-aminoisonicotinate (0.768 g, 5.05 mmol) in PPA (2.5 mL) and 1,2-dichloroethane (5 mL) was stirred at 85° C. for 18 hours. The reaction mixture was then cooled to ambient temperature. A chilled saturated sodium carbonate solution was added to adjust pH to 8. The resulting mixture was extracted with ethyl acetate (4×100 mL). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate. After filtration and concentration, the crude product was purified by silica gel chromatography purification to afford 157 mg of desired product.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (4×100 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration and concentration
  5. customthe crude product was purified by silica gel chromatography purification

Sources & evidence

ORD record
ord-1f23e14733cf4faf95513b1b009ab46e
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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