Water → HCID 21850842, compound

HRID 618447Notes

Reaction equation

HRID 618447 reaction equation
[C:1]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10]([O:17][CH3:18])[N:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28].O>ClCCl>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[O:16][S:27]([CH3:26])(=[O:29])=[O:28])=[CH:13][CH:12]=[N:11][C:10]=2[O:17][CH3:18])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21850846HCID 21850846, compound

Product 1

HCID 21850842HCID 21850842, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4.93 g of 3-butyryl 8-methoxy-1,7-naphthyridin-4(1H)-one and 4.2 ml of triethylamine were dissolved into 70 ml of dichloromethane, and a solution of methanesulfonyl chloride (1.85 ml) in dichloromethane (10 ml) was added dropwise at a temperature of 0° C. to 5° C. The resulting mixture was stirred for 1 hour at the same temperature. Water was added, and the resulting mixture was extracted with dichloromethan three times, and the organic phase was washed with water and then brine, dried over magnesium sulfate and distilled under reduced pressure. Ether was added to the residue to give 4.61 g (71%) of the titled compound as yellow crystals.

Workup

  1. extractionthe resulting mixture was extracted with dichloromethan three times
  2. washthe organic phase was washed with water
  3. dry with materialbrine, dried over magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. additionEther was added to the residue

Sources & evidence

ORD record
ord-cff175f9aa074bd08ef38925d3227988
Source dataset
uspto-grants-1999_09
Patent number
US05952504

Reaction notes

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