Water → HCID 57625404, compound

HRID 655626Notes

Reaction equation

HRID 655626 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]([NH:22][S:23]([C:26]3[CH:27]=[N:28][C:29]([CH2:32]O)=[CH:30][CH:31]=3)(=[O:25])=[O:24])=[N:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.S(Cl)([Cl:36])=O.O.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[Cl:36][CH2:32][C:29]1[N:28]=[CH:27][C:26]([S:23]([NH:22][C:13]2[C:12]([NH:11][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=3)=[N:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)(=[O:25])=[O:24])=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 16045752HCID 16045752, compound

Product 1

HCID 57625404HCID 57625404, compoundYield 108.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-{3-[(3,5-dimethoxyphenyl)amino]quinoxalin-2-yl}-6-(hydroxymethyl)pyridine-3-sulfonamide (90 mg; 0.19 mmol; 1 eq.) is dissolved in CHCl3 (10 ml) at rt. Thionyl chloride (0.05 ml; 0.39 mmol; 2 eq.) is added and reaction mixture is stirred for 1 h30. Water and aqueous NaHCO3 are added and the product is extracted with DCM. The organic phase is dried over magnesium sulfate and the solvent is evaporated under reduced pressure to afford 100 mg (108%) of the title compound as a powder. It was used as such in the next step. HPLC (max plot) 35%; Rt 4.78 min, LC/MS: (ES+) 486.22, (ES−) 484.22.

Workup

  1. customreaction mixture
  2. extractionthe product is extracted with DCM
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-0ecc7e77b7594250ab7565e8dd6ed120
Source dataset
uspto-grants-2011_12
Patent number
US08071597B2

Reaction notes

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