Water → Ethanesulfonic acid [5-(5-methyl-6-oxo-5,6,7,8-tetrahydro-[1,5]naphthyridin-2-yl)-pyridin-3-ylmethyl]-amide

HRID 1774800Notes

Reaction equation

HRID 1774800 reaction equation
[CH2:1]([S:3]([NH2:6])(=[O:5])=[O:4])[CH3:2].[H-].[Na+].Cl[CH2:10][C:11]1[CH:12]=[C:13]([C:17]2[N:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]([CH3:27])[C:22](=[O:28])[CH2:21][CH2:20]3)[CH:14]=[N:15][CH:16]=1.O>CN(C=O)C>[CH3:27][N:23]1[C:22](=[O:28])[CH2:21][CH2:20][C:19]2[N:18]=[C:17]([C:13]3[CH:12]=[C:11]([CH2:10][NH:6][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH:16]=[N:15][CH:14]=3)[CH:26]=[CH:25][C:24]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 73702EthanesulfonamideHCID 866791636-(5-chloromethyl-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one

Product 1

HCID 71533397Ethanesulfonic acid [5-(5-methyl-6-oxo-5,6,7,8-tetrahydro-[1,5]naphthyridin-2-yl)-pyridin-3-ylmethyl]-amideYield 7.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of ethanesulfonic acid amide (118 mg, 1.08 mmol) in DMF (5.0 mL) was added 60% NaH (35 mg, 0.81 mmol) at RT and the resulting reaction mixture was stirred for 0.5 hour before 6-(5-chloromethyl-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-[1,5]naphthyridin-2-one (156 mg, 0.54 mmol) was added. After continued stirring at RT for additional 2 hours, water (1.0 mL) was added. After extraction with EtOAc, the organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product which was purified by prep-HPLC to give title compound (15 mg, 7.7%) as a light yellow solid. MS: 361.1 (M+H+).

Workup

  1. customthe resulting reaction mixture
  2. additionwas added
  3. extractionAfter extraction with EtOAc
  4. washthe organic layer was washed with brine
  5. customdried over anhy
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated in vacuo
  8. customto give a crude product which
  9. customwas purified by prep-HPLC

Sources & evidence

ORD record
ord-b2b2e578d7db42f48f5c6560b60c77aa
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

Loading…