Hydrochloric Acid → HCID 46893808, compound

HRID 1397855Notes

Reaction equation

HRID 1397855 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:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[S:31](Cl)(=[O:33])=[O:32].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:31]([C:25]4[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:24]=4[F:23])(=[O:33])=[O:32])[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 27369112,5-Difluorobenzenesulfonyl chlorideHCID 66647207HCID 66647207, compound

Product 1

HCID 46893808HCID 46893808, compoundYield 66.1%

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, 100 mg, 0.335 mmol) in 2.7 mL of tetrahydrofuran, 0.24 mL of pyridine was added. 2,5-Difluoro-benzenesulfonyl chloride (29, 107 mg, 0.503 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-0004, 105 mg). MS(ESI)[M+H+]+=475.0.

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-d463254c9ca34bde93149cdac11afece
Source dataset
uspto-grants-2014_12
Patent number
US08901301B2

Reaction notes

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