Hydrochloric Acid → HCID 70829816, compound

HRID 1397839Notes

Reaction equation

HRID 1397839 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([C:10]#[N:11])[CH:9]=[C:4]2[CH:3]=[CH:2]1.[F:12][C:13]1[C:18]([CH:19]=[O:20])=[C:17]([F:21])[CH:16]=[CH:15][C:14]=1[NH:22][S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24].[OH-].[K+].Cl>CO>[C:10]([C:8]1[CH:9]=[C:4]2[C:3]([CH:19]([OH:20])[C:18]3[C:13]([F:12])=[C:14]([NH:22][S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])[CH:15]=[CH:16][C:17]=3[F:21])=[CH:2][NH:1][C:5]2=[N:6][CH:7]=1)#[N:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 117883551H-Pyrrolo[2,3-b]pyridine-5-carbonitrileHCID 53419003N-(2,4-Difluoro-3-formylphenyl)-1-propanesulfonamide

Product 1

HCID 70829816HCID 70829816, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (13, 301 mg, 2.10 mmol), propane-1-sulfonic acid (2,4-difluoro-3-formyl-phenyl)-amide (12, 1.11 g, 4.20 mmol) and potassium hydroxide (354 mg, 6.31 mmol) were combined in a vial with 4.2 mL of methanol. The reaction was stirred for 3 hours at room temperature. The reaction solution was neutralized with 0.1 N aqueous hydrochloric acid and extracted 3× with ethyl acetate. The organic layers were combined and washed with brine, then dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. This was allowed to stir over the weekend at room temperature, then extracted with ethyl acetate and water. The organic layer was washed with brine and then dried over magnesium sulfate, filtered, and the solvents were removed from the filtrate under vacuum. The resulting material was purified by silica gel column chromatography eluting with ethyl acetate in hexanes to provide the desired compound (14, 315 mg). MS(ESI) [M−H+]−=405.3.

Workup

  1. extractionextracted 3× with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. stirringto stir over the weekend at room temperature
  7. extractionextracted with ethyl acetate and water
  8. washThe organic layer was washed with brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customthe solvents were removed from the filtrate under vacuum
  12. customThe resulting material was purified by silica gel column chromatography
  13. washeluting with ethyl acetate in hexanes

Sources & evidence

ORD record
ord-9002dd4896b842699aefa2388b23a21a
Source dataset
uspto-grants-2014_12
Patent number
US08901301B2

Reaction notes

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