Hydrochloric Acid → HCID 46913051, compound

HRID 1397856Notes

Reaction equation

HRID 1397856 reaction equation
[NH2:1][C:2]1[C:3]([F:22])=[C:4]([C:18]([F:21])=[CH:19][CH:20]=1)[C:5]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([C:16]#[N:17])[CH:14]=2)[NH:9][CH:8]=1)=[O:6].[F:23][C:24]1[CH:25]=[C:26]([S:30](Cl)(=[O:32])=[O:31])[CH:27]=[CH:28][CH:29]=1.Cl>O1CCCC1.N1C=CC=CC=1>[C:16]([C:13]1[CH:14]=[C:15]2[C:7]([C:5]([C:4]3[C:3]([F:22])=[C:2]([NH:1][S:30]([C:26]4[CH:27]=[CH:28][CH:29]=[C:24]([F:23])[CH:25]=4)(=[O:32])=[O:31])[CH:20]=[CH:19][C:18]=3[F:21])=[O:6])=[CH:8][NH:9][C:10]2=[N:11][CH:12]=1)#[N:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 66647207HCID 66647207, compound

Product 1

HCID 46913051HCID 46913051, compoundYield 83.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 3-(3-amino-2,6-difluoro-benzoyl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (28, 130 mg, 0.436 mmol) in 3.5 mL of tetrahydrofuran, 0.31 mL of pyridine was added. 3-Fluoro-benzenesulfonyl chloride (30, 127 mg, 0.654 mmol) was added and the solution was stirred at room temperature for 48 hours. The reaction mixture was poured into 1 M aqueous hydrochloric acid and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under vacuum. The crude material was purified by silica gel column chromatography eluting with ethyl acetate and hexane. Appropriate fractions were combined and the solvent removed under reduced pressure to provide the desired compound (P-0005, 167 mg). MS(ESI)[M+H+]+=457.6.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under vacuum
  6. customThe crude material was purified by silica gel column chromatography
  7. washeluting with ethyl acetate and hexane
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-c2c45466c03442199f227399c6678a6f
Source dataset
uspto-grants-2014_12
Patent number
US08901301B2

Reaction notes

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