Methanol → 3-Acetyl-2-methyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydro-1,6-naphthyridin-5-yl ethane-sulfonate

HRID 1951407Notes

Reaction equation

HRID 1951407 reaction equation
[C:1]([C:4]1[CH:13]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:23]=2[O:22][C:21]([CH3:24])=[CH:20][C:19]3=[O:25])[C:12]2[C:11](=[O:26])[NH:10][CH:9]=[CH:8][C:7]=2[NH:6][C:5]=1[CH3:27])(=[O:3])[CH3:2].[CH2:28]([S:30](Cl)(=[O:32])=[O:31])[CH3:29].CO>N1C=CC=CC=1>[CH2:28]([S:30]([O:26][C:11]1[N:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[CH:13]([C:14]1[CH:15]=[CH:16][CH:17]=[C:18]3[C:23]=1[O:22][C:21]([CH3:24])=[CH:20][C:19]3=[O:25])[C:4]([C:1](=[O:3])[CH3:2])=[C:5]([CH3:27])[NH:6]2)(=[O:32])=[O:31])[CH3:29]

Participants

5

Reactant 3

HCID 887MethanolHCID 11667Ethanesulfonyl chlorideHCID 596030093-Acetyl-2-methyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-4,6-dihydro-1,6-naphthyridin-5(1H)-one

Product 1

HCID 247984213-Acetyl-2-methyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydro-1,6-naphthyridin-5-yl ethane-sulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

133 mg (0.367 mmol) of 3-acetyl-2-methyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-4,6-dihydro-1,6-naphthyridin-5(1H)-one are suspended in pyridine (5 ml), and 700 (0.73 mmol) of ethanesulfonyl chloride are added. The suspension is stirred at RT for 3 h (during which the precursor dissolves), and then mixed with methanol and concentrated. The residue is purified by preparative HPLC to result in 63 mg (43% of theory) of the title compound as a white solid.

Workup

  1. dissolutionprecursor dissolves), and
  2. concentrationconcentrated
  3. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-05f5eff3d98041859db2064ae48d121c
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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