Ethyl Acetate → HCID 21186249, compound

HRID 361418Notes

Reaction equation

HRID 361418 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[CH2:3][CH2:4][O:5][CH2:6]Cl.[Cl:10][C:11]1[C:16]([S:17]([NH:20][C:21]2[C:26]([O:27][CH3:28])=[N:25][C:24]([CH3:29])=[CH:23][N:22]=2)(=[O:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=1.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>CN(C=O)C>[Cl:10][C:11]1[C:16]([S:17]([N:20]([C:21]2[C:26]([O:27][CH3:28])=[N:25][C:24]([CH3:29])=[CH:23][N:22]=2)[CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:9])([CH3:8])[CH3:1])(=[O:18])=[O:19])=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 21186216HCID 21186216, compound

Product 1

HCID 21186249HCID 21186249, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(Trimethylsilyl)ethoxymethyl chloride (0.315 ml) was added dropwise to a stirred solution of 2-chloro-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.47 g) and N,N-diisopropylethylamine (0.347 ml) in dry DMF (7 ml) at -15° C. Stirring was continued for 40 minutes at this temperature after the addition was complete. Ethyl acetate (40 ml) was added and the mixture was washed with water (3×15 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 0-30% ethyl acetate/hexane through a silica gel Mega Bond Elut column to give 2-chloro-N-(3-methoxy-5-methylpyrazin-2-yl)-N-[2-(trimethylsilyl)ethoxymethyl]pyridine-3-sulphonamide (0.462 g) as an oil; 1H NMR (CDCl3): 0.0 (s, 9 H), 0.85 (t, 2 H), 2.5 (s, 3 H), 3.75 (t, 2 H), 3.8 (s, 3 H), 5.3 (s, 2 H), 7.3 (dd, 1 H), 7.8 (s, 1 H), 8.4 (dd, 1 H), 8.5 (dd, 1 H); mass spectrum (+ve ESP): 403 (M+H)+.

Workup

  1. additionafter the addition
  2. washthe mixture was washed with water (3×15 ml) and saturated sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. customVolatile material was removed by evaporation
  5. customthe residue was purified by gradient elution with 0-30% ethyl acetate/hexane through a silica gel Mega Bond Elut column

Sources & evidence

ORD record
ord-5811fc872e854436a0a6ec0d47d993ce
Source dataset
uspto-grants-1999_02
Patent number
US05866568

Reaction notes

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