Hydrochloric Acid → HCID 46913145, compound

HRID 1397857Notes

Reaction equation

HRID 1397857 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].[N:23]1([S:28](Cl)(=[O:30])=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24]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:28]([N:23]4[CH2:27][CH2:26][CH2:25][CH2:24]4)(=[O:30])=[O:29])[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 64839021-Pyrrolidinesulfonyl chlorideHCID 66647207HCID 66647207, compound

Product 1

HCID 46913145HCID 46913145, compoundYield 24.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To 3-(3-amino-2,6-difluoro-benzoyl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (28, 354 mg, 1.19 mmol) in 9.5 mL of tetrahydrofuran, 0.84 mL of pyridine was added. Pyrrolidine-1-sulfonyl chloride (31, 403 mg, 2.37 mmol) was added and the solution was stirred at 60° C. 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-0006, 127 mg). MS(ESI)[M+H+]+=432.1.

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-27d31fbefa7848ce8b2eac00bf76b8b2
Source dataset
uspto-grants-2014_12
Patent number
US08901301B2

Reaction notes

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