Hydrochloric Acid → HCID 86647372, compound

HRID 1397848Notes

Reaction equation

HRID 1397848 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])=[CH:17][CH:16]=[CH:15][C:14]=1[NH:21][S:22]([CH2:25][CH2:26][CH3:27])(=[O:24])=[O:23].[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:21][S:22]([CH2:25][CH2:26][CH3:27])(=[O:24])=[O:23])[CH:15]=[CH:16][CH:17]=3)=[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 58086814Propane-1-sulfonic acid (2-fluoro-3-formyl-phenyl)-amide

Product 1

HCID 86647372HCID 86647372, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (13, 132 mg, 0.923 mmol), propane-1-sulfonic acid (2-fluoro-3-formyl-phenyl)-amide (22, 151 mg, 0.616 mmol) and potassium hydroxide (104 mg, 1.85 mmol) were combined in a round bottom flask with 1.2 mL of methanol. The reaction was stirred for 2 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. The resulting material was purified by silica gel column chromatography eluting with ethyl acetate and dichloromethane to provide the desired compound (23, 79 mg). MS(ESI) [M−H+]31 =387.5.

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. customThe resulting material was purified by silica gel column chromatography
  7. washeluting with ethyl acetate and dichloromethane

Sources & evidence

ORD record
ord-5baf545248db4e23b4b5221fae0da266
Source dataset
uspto-grants-2014_12
Patent number
US08901301B2

Reaction notes

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