Water → HCID 57625404, compound

HRID 331199Notes

Reaction equation

HRID 331199 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-225e074baa234804a6a58c616cfa20fa
Source dataset
uspto-grants-2014_11
Patent number
US08877757B2

Reaction notes

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