Water → HCID 21850843, compound

HRID 618444Notes

Reaction equation

HRID 618444 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[NH:11][CH:10]=[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]2=[O:18].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28].O>ClCCl>[CH3:26][S:27]([O:18][C:8]1[C:7]2[C:12](=[C:3]([O:2][CH3:1])[N:4]=[CH:5][CH:6]=2)[N:11]=[CH:10][C:9]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14])(=[O:29])=[O:28]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21850845HCID 21850845, compound

Product 1

HCID 21850843HCID 21850843, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4.96 g of ethyl 8-methoxy-1,7-naphthyridin-4(1H)-one-3-carboxylate 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 dichloromethane 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 4.4 g (67%) of the titled compound as yellow crystals.

Workup

  1. extractionthe resulting mixture was extracted with dichloromethane 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-d127e331ca80444792e7a8a6f3f7eb9b
Source dataset
uspto-grants-1999_09
Patent number
US05952504

Reaction notes

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