Tetrahydrofuran → HCID 59168220, compound

HRID 1444031Notes

Reaction equation

HRID 1444031 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:18]([O:19][CH3:20])=[N:17][C:16]([CH2:21][OH:22])=[C:15]([Cl:23])[N:14]=1)(=[O:11])=[O:10].O1CCC[CH2:25]1>[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:18]([O:19][CH3:20])=[N:17][C:16]([CH2:21][O:22][CH3:25])=[C:15]([Cl:23])[N:14]=1)(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 59168106HCID 59168106, compound

Product 1

HCID 59168220HCID 59168220, compound

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

To a stirred solution of 2,3-dichloro-N-[6-chloro-5-(hydroxymethyl)-3-methoxy-2-pyrazinyl]benzenesulphonamide (Example 127) (0.1 g) in tetrahydrofuran (3 mL) was added manganese dioxide (0.131 g) and the resulting suspension was stirred for 20 h, filtered and concentrated. The residue was taken up into methanol (3 mL) and acetic acid (0.1 mL). To this solution was added ethylamine hydrochloride (0.081 g) and sodium cyanoborohydride (0.051 g). The resulting mixture was stirred for 20 h and concentrated onto silical gel (1 g) and eluting with methanol/dichloromethane mixtures to afford the titled compound (0.029 g) as a white solid.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. additionTo this solution was added ethylamine hydrochloride (0.081 g) and sodium cyanoborohydride (0.051 g)
  4. stirringThe resulting mixture was stirred for 20 h
  5. concentrationconcentrated onto silical gel (1 g)
  6. washeluting with methanol/dichloromethane

Sources & evidence

ORD record
ord-579454a78b4a4f518255622c6d25e722
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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