Ethyl Acetate → 4-chloro-N-(3-methoxy-5-methylpyrazin-2-yl)-N-[2-(trimethylsilyl)ethoxymethyl]pyridine-3-sulphonamide

HRID 361425Notes

Reaction equation

HRID 361425 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[CH2:3][CH2:4][O:5][CH2:6]Cl.[Cl:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[S:17]([NH:20][C:21]1[C:26]([O:27][CH3:28])=[N:25][C:24]([CH3:29])=[CH:23][N:22]=1)(=[O:19])=[O:18].C(OCC)(=O)C>CN(C=O)C>[Cl:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[S:17]([N:20]([C:21]1[C:26]([O:27][CH3:28])=[N:25][C:24]([CH3:29])=[CH:23][N:22]=1)[CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:9])([CH3:8])[CH3:1])(=[O:18])=[O:19]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 211862364-chloro-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide

Product 1

HCID 211862784-chloro-N-(3-methoxy-5-methylpyrazin-2-yl)-N-[2-(trimethylsilyl)ethoxymethyl]pyridine-3-sulphonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-5 °C

Procedure

2-(Trimethylsilyl)ethoxymethyl chloride (0.22 ml) was added dropwise over 5 minutes to a stirred solution of 4-chloro-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.306 g) and N,N-diisopropylethylaminc (0.21 ml) in dry DMF (1 ml) at -15° C. The resultant solution was allowed to warm to -5° C. over 40 minutes then ethyl acetate (30 ml) was added and the mixture was washed with 2M hydrochloric acid (30 ml), water (30 ml) and saturated sodium chloride solution and then dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by gradient elution with 30-50% ethyl acetate/hexane through a silica gel Mega Bond Elut column to give 4-chloro-N-(3-methoxy-5-methylpyrazin-2-yl)-N-[2-(trimethylsilyl)ethoxymethyl]pyridine-3-sulphonamide (0.266 g) as an oil; 1H NMR (d6 -DMSO): -0.1 (s, 9 H), 0.7 (t, 2 H), 2.45 (s, 3 H), 3.6 (t, 2 H), 3.85 (s, 3 H), 5.2 (s, 2 H), 7.8 (d, 1 H), 8.0 (s, 1 H), 8.8 (d, 1 H), 9.1 (s, 1 H); mass spectrum (+ve FAB, DMSO/Glycerol): 445 (M+H)+.

Workup

  1. washthe mixture was washed with 2M hydrochloric acid (30 ml), water (30 ml) and saturated sodium chloride solution
  2. dry with materialdried (MgSO4)
  3. customVolatile material was removed by evaporation
  4. customthe residue was purified by gradient elution with 30-50% ethyl acetate/hexane through a silica gel Mega Bond Elut column

Sources & evidence

ORD record
ord-a7768cba59324a329494a963aced634d
Source dataset
uspto-grants-1999_02
Patent number
US05866568

Reaction notes

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