Cesium carbonate → 4-[5-(2,3-Dichlorobenzenesulphonylamino)-6-methoxy-2-pyrazinyloxy]benzoic acid

HRID 1443990Notes

Reaction equation

HRID 1443990 reaction equation
[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)(C)(C)[CH3:2].Br[C:16]1[N:17]=[C:18]([O:42][CH3:43])[C:19]([N:22](COCC[Si](C)(C)C)[S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=2[Cl:33])(=[O:25])=[O:24])=[N:20][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.C(OCC)(=O)C>[C:6]([O:5][CH2:1][CH3:2])(=[O:14])[CH3:7].[CH3:10][CH2:9][CH2:8][CH:7]([CH3:12])[CH3:6].[Cl:33][C:27]1[C:28]([Cl:32])=[CH:29][CH:30]=[CH:31][C:26]=1[S:23]([NH:22][C:19]1[N:20]=[CH:21][C:16]([O:13][C:10]2[CH:9]=[CH:8][C:7]([C:6]([OH:5])=[O:14])=[CH:12][CH:11]=2)=[N:17][C:18]=1[O:42][CH3:43])(=[O:25])=[O:24]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 117640tert-Butyl 4-hydroxybenzoateHCID 59168156N-(5-Bromo-3-methoxy-2-pyrazinyl)-2,3-dichloro-N-[{2-(trimethylsilanyl)ethoxy}methyl]benzenesulphonamide

Product 2

HCID 102172984-[5-(2,3-Dichlorobenzenesulphonylamino)-6-methoxy-2-pyrazinyloxy]benzoic acidHCID 21882781Isohexane ethyl acetate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Hydroxybenzoic acid tert butyl ester (0.13 g), N-(5-bromo-3-methoxy-2-pyrazinyl)-2,3-dichloro-N-[{2-(trimethylsilanyl)ethoxy}methyl]benzenesulphonamide (Example 55 part a) (0.35 g) and caesium carbonate (0.42 g) in acetonitrile (10 mL) was heated at 50° C. After 12 h, the mixture was diluted with ethyl acetate, washed with water, dried (MgSO4) and evaporated. Chromatography on silica gel eluting with ethyl acetate/isohexane mixtures gave the title compound protected with the SEM group and tert butyl group as an oil. The oil was dissolved in trifluoroacetic acid (2.0 mL) and stirred at room temperature for 3 h.

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-8d80e8d66a0540ac95b0b7753090fc66
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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