Hydrochloric Acid → HCID 58266643, compound

HRID 1505966Notes

Reaction equation

HRID 1505966 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[C:16]1([S:22]([N:25]2[C:29]3[CH:30]=[N:31][C:32]([C:35]#[N:36])=[C:33](O)[C:28]=3[C:27]3[CH:37]=[CH:38][CH:39]=[N:40][C:26]2=3)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N1C=CC=CC=1.Cl>C(Cl)Cl>[C:16]1([S:22]([N:25]2[C:29]3[CH:30]=[N:31][C:32]([C:35]#[N:36])=[C:33]([O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])[C:28]=3[C:27]3[CH:37]=[CH:38][CH:39]=[N:40][C:26]2=3)(=[O:24])=[O:23])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 582663029-Benzenesulfonyl-5-hydroxy-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

Product 1

HCID 58266643HCID 58266643, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (0.91 g, 0.54 mL, 3.22 mmol) was added dropwise to a suspension of 9-benzenesulfonyl-5-hydroxy-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (1.03 g, 2.93 mmol) in pyridine (1.2 mL, 14.7 mmol) and dry DCM (20 mL) at 0° C. The reaction mixture was then allowed to warm to ambient temperature and stirred for 2 h. The reaction mixture was treated with 1N hydrochloric acid (10 mL) and the phases were separated. The aqueous phase was extracted with DCM (2×10 mL), the combined organic phase was dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant residue was purified by chromatography (silica, 5 g column, Si-SPE, DCM) to afford the title compound as a white solid (855 mg, 60%). LCMS (Method B): RT=4.22 min, M+H+=483.

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with DCM (2×10 mL)
  3. dry with materialthe combined organic phase was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by chromatography (silica, 5 g column, Si-SPE, DCM)

Sources & evidence

ORD record
ord-b72f30fb53db4510aad00d542b65c5ec
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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