1-Propanesulfonyl chloride → 3-Acetyl-2-methyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydro-1,6-naphthyridin-5-yl propanesulfonate

HRID 1951409Notes

Reaction equation

HRID 1951409 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:31](Cl)(=[O:33])=[O:32])[CH2:29][CH3:30]>>[CH2:28]([S:31]([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:33])=[O:32])[CH2:29][CH3:30]

Participants

3

Reactant 2

HCID 662791-Propanesulfonyl 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 247984223-Acetyl-2-methyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydro-1,6-naphthyridin-5-yl propanesulfonate

Procedure

The title compound is prepared in analogy to example 10 from 50 mg (0.13 mmol) of 3-acetyl-2-methyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-4,6-dihydro-1,6-naphthyridin-5(1H)-one and 17 μl (0.15 mmol) of propanesulfonyl chloride. 46 mg (71% of theory) of the product are obtained as a pale yellow solid.

Workup

  1. custom46 mg (71% of theory) of the product are obtained as a pale yellow solid

Sources & evidence

ORD record
ord-5849eb0ebed2448b9b4b1af260ae4198
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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