Triethylamine → 4-(7-Oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yloxy)butyl methanesulfonate

HRID 1750076Notes

Reaction equation

HRID 1750076 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[N:16]=[C:15]2[C:10]([CH2:11][CH2:12][C:13](=[O:17])[NH:14]2)=[CH:9][CH:8]=1.CCN(CC)CC.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl>[CH3:25][S:26]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[CH2:11][CH2:12][C:13](=[O:17])[NH:14][C:15]=2[N:16]=1)(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 210738467-(4-Hydroxybutoxy)-3,4-dihydro-1,8-naphthyridin-2(1H)-one

Product 1

HCID 870843174-(7-Oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yloxy)butyl methanesulfonateYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of intermediate 11 (140 mg, 0.593 mmol), Et3N (240 mg, 2.37 mmol) and methylsulfonyl chloride (102 mg, 0.89 mmol) was dissolved in DCM and the solution was stirred for 6 h at rt. The solution was then washed with water, brine, and dried over anhydrous Na2SO4. After filtration, the solvent was evaporated in vacuo to give 4-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yloxy)butyl methanesulfonate (intermediate 12) (180 mg, 96%) as a yellow solid.

Workup

  1. washThe solution was then washed with water, brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationAfter filtration
  4. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-06e46d446cd4498aabe326cecd6e3edd
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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