Triethylamine → HCID 53353586, compound

HRID 710584Notes

Reaction equation

HRID 710584 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[C:10](=[O:23])[N:11]([CH3:22])[C:12]3[C:17]([CH:18]=2)=[CH:16][N:15]=[C:14]([NH:19][CH2:20][CH3:21])[CH:13]=3)[C:5]([F:24])=[CH:4][N:3]=1.C(N(CC)CC)C.[CH2:32]([S:35](Cl)(=[O:37])=[O:36])[CH2:33][CH3:34].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:20]([NH:19][C:14]1[CH:13]=[C:12]2[C:17]([CH:18]=[C:9]([C:6]3[C:5]([F:24])=[CH:4][N:3]=[C:2]([NH:1][S:35]([CH2:32][CH2:33][CH3:34])(=[O:37])=[O:36])[C:7]=3[F:8])[C:10](=[O:23])[N:11]2[CH3:22])=[CH:16][N:15]=1)[CH3:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 662791-Propanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 67378126HCID 67378126, compound

Product 1

HCID 53353586HCID 53353586, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution 3-(2-Amino-3,5-difluoropyridin-4-yl)-7-(ethylamino)-1-methyl-1,6-naphthyridin-2(1H)-one (15 mg, 0.05 mmol), triethylamine (3 ml), and DCM (10 mL) was treated with n-propanesulfonyl chloride (0.05 ml, 0.4 mmol) at 0° C. The mixture was allowed to warm to rt and was stirred for 16 h. Aqueous sodium bicarbonate solution was added, and the mixture was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was dissolved in methanol (10 mL) and potassium carbonate (2 g) was added. The mixture was stirred at room temperature for 2 h. Water was added and the mixture was extracted with ethyl acetate, then the combined organic extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was chromatographed on silica gel (2% to 3% methanol in DCM eluant) to provide the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in methanol (10 mL)
  6. additionpotassium carbonate (2 g) was added
  7. stirringThe mixture was stirred at room temperature for 2 h
  8. additionWater was added
  9. extractionthe mixture was extracted with ethyl acetate
  10. washthe combined organic extracts were washed with brine
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customThe residue was chromatographed on silica gel (2% to 3% methanol in DCM eluant)

Sources & evidence

ORD record
ord-10340ad38f7441fc98f81b4b5b1c28ad
Source dataset
uspto-grants-2015_11
Patent number
US09181238B2

Reaction notes

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