Hydrochloric Acid → HCID 16045008, compound

HRID 237357Notes

Reaction equation

HRID 237357 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][CH:29]=[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.CS(C)=[O:34].[OH-].[Na+].Cl>O>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([NH:11][C:12]2[C:13]([NH:22][S:23]([C:26]3[CH:31]=[CH:30][C:29](=[O:34])[NH:28][CH:27]=3)(=[O:24])=[O:25])=[N:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 16045229HCID 16045229, compound

Product 1

HCID 16045008HCID 16045008, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-(3-(3,5-dimethoxyphenylamino)quinoxalin-2-yl)pyridine-3-sulfonamide (220 mg, 0.47 mmol), DMSO (5 mL), and 3N NaOH (5 mL) are combined and heated to 100 C. overnight with stirring. Upon cooling to room temperature, the reaction mixture was diluted with H2O and the pH was adjusted to 7.0 with 1N HCl. The resulting solid was filtered, washed with H2O, and air-dried. The solid was then sonicated in EtOAc, filtered, washed with EtOAc, and dried under high vacuum to give N-(3-(3,5-dimethoxyphenylamino)quinoxalin-2-yl)-6-oxo-1,6-dihydropyridine-3-sulfonamide (190 mg, 90%). 1H NMR (400 MHz, DMSO-d6) δ 12.23 (br s, 1H), 12.10 (br s, 1H), 8.97 (s, 1H), 8.23 (s, 1H), 7.95 (m, 2H), 7.59 (m, 1H), 7.37 (m, 4H), 6.43 (d, 1H), 6.25 (s, 1H), 3.77 (s, 6H). MS (EI) for C21H19N5O5S: 454.0 (MH+).

Workup

  1. temperatureheated to 100 C
  2. filtrationThe resulting solid was filtered
  3. washwashed with H2O
  4. customair-dried
  5. customThe solid was then sonicated in EtOAc
  6. filtrationfiltered
  7. washwashed with EtOAc
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-58b34bbc590f4ff3a1c5dee5c825d0ea
Source dataset
uspto-grants-2014_02
Patent number
US08642584B2

Reaction notes

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