Hydrochloric Acid → HCID 68323816, compound

HRID 573645Notes

Reaction equation

HRID 573645 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]3[S:19][C:20]([CH3:24])=[C:21]([C:22]#[N:23])[C:13]=23)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.CS(C)=[O:27].[OH-].[Na+].Cl>O>[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]3[S:19][C:20]([CH3:24])=[C:21]([C:22]([NH2:23])=[O:27])[C:13]=23)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 53250694HCID 53250694, compound

Product 1

HCID 68323816HCID 68323816, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-chloro-N-(3-cyano-2,6-dimethylthieno[2,3-b]pyridin-4-yl)benzenesulfonamide (Example 73) (119 mg, 0.315 mmol), DMSO (3 mL) and aqueous NaOH (3M) (1.05 mL, 3.15 mmol) was stirred at 150° C. for 5 h. The mixture was then cooled and acidified with 5M HCl to pH 3-4. Water (20 mL) was added and the mixture extracted with ethyl acetate (3×10 mL). The organic layer was then dried over MgSO4, filtered and concentrated. The residue was purified by normal phase chromatography, eluting with a gradient of 0-10% MeOH in DCM, and then further triturated with MeOH, to give the title compound (69 mg). LCMS (A) m/z: 396 [M+1]+, Rt 1.13 min (acidic).

Workup

  1. temperatureThe mixture was then cooled
  2. extractionthe mixture extracted with ethyl acetate (3×10 mL)
  3. dry with materialThe organic layer was then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by normal phase chromatography
  7. washeluting with a gradient of 0-10% MeOH in DCM
  8. customfurther triturated with MeOH

Sources & evidence

ORD record
ord-aa0cd570fb8f41378aa2aa4b66658e1b
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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