2,3-dichloro-N-(3,5-dichloro-2-pyrazinyl)benzenesulphonamide → N-[3-[(2-amino-4-oxazolyl)methoxy]-5-chloro-2-pyrazinyl]-2,3-dichlorobenzenesulphonamide

HRID 1444087Notes

Reaction equation

HRID 1444087 reaction equation
C(OC(=O)[NH:7][C:8]1[O:9][CH:10]=[C:11]([CH2:13][OH:14])[N:12]=1)(C)(C)C.[Cl:16][C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=1[S:24]([NH:27][C:28]1[C:33](Cl)=[N:32][C:31]([Cl:35])=[CH:30][N:29]=1)(=[O:26])=[O:25]>>[NH2:7][C:8]1[O:9][CH:10]=[C:11]([CH2:13][O:14][C:33]2[C:28]([NH:27][S:24]([C:18]3[CH:19]=[CH:20][CH:21]=[C:22]([Cl:23])[C:17]=3[Cl:16])(=[O:26])=[O:25])=[N:29][CH:30]=[C:31]([Cl:35])[N:32]=2)[N:12]=1

Participants

3

Reactant 2

HCID 101263402,3-dichloro-N-(3,5-dichloro-2-pyrazinyl)benzenesulphonamideHCID 45092179tert-Butyl (4-(hydroxymethyl)oxazol-2-yl)carbamate

Product 1

HCID 10310503N-[3-[(2-amino-4-oxazolyl)methoxy]-5-chloro-2-pyrazinyl]-2,3-dichlorobenzenesulphonamide

Procedure

Prepared by the method of Example 112 using (4-hydroxymethyl-2-oxazolyl)carbamic acid tert-butyl ester (Example 212a) (0.12 g) and 2,3-dichloro-N-(3,5-dichloro-2-pyrazinyl)benzenesulphonamide (Example 74) (0.21 g). Purification was by silica gel chromatography eluting with ethyl acetate/iso-hexane mixtures to give the title compound with the BOC (tert-butyl carbonyl) attached (0.11 g). This compound was dissolved in trifluoroacetic acid (1.5 mL) and dichloromethane (1.5 mL). After 2 h, the solution was evaporated. Purification was by silica gel chromatography eluting with ethyl acetate/iso-hexane mixtures to give the title compound. Yield 0.08 g.

Workup

  1. customPurification
  2. washeluting with ethyl acetate/iso-hexane

Sources & evidence

ORD record
ord-4a4421fd9da24a00b6c627c64bbfad4c
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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