Hydrochloric Acid → HCID 66702053, compound

HRID 424654Notes

Reaction equation

HRID 424654 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9](Cl)(=[O:11])=[O:10])#[N:2].[CH2:13]([S:20][C:21]1[N:26]=[C:25]([NH:27]S(C)(=O)=O)[CH:24]=[C:23]([NH:32][C@H:33]([CH3:36])[CH2:34]O)[N:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[F-].[CH2:38]([N+](CCCC)(CCCC)CCCC)CCC.Cl>N1C=CC=CC=1>[CH2:13]([S:20][C:21]1[N:26]=[C:25]([NH:27][S:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:1]#[N:2])(=[O:11])=[O:10])[CH:24]=[C:23]([NH:32][C@H:33]([CH3:36])[CH2:34][CH3:38])[N:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5223472-Cyanobenzenesulfonyl ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 57833159HCID 57833159, compound

Product 1

HCID 66702053HCID 66702053, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Cyanobenzenesulfonyl chloride (0.30 g) was added to the solution of the subtitle product of Example 3 step (0.1 g) in pyridine (1 ml) and N,N-dimethylaminopyridine (30 mg). The reaction mixture was stirred for 4 h. To the reaction mixture was added tetrabutylammonium fluoride (4 ml, 1M in THF) and stirred for 16 h. To this reaction was added aqueous hydrochloric acid (1M, 30 ml). The solvent was evaporated and the residue diluted in EtOAc (100 ml). This was washed with H2O (3×20 ml) and brine (10 ml). The organic layer was dried (MgSO4) and concentrated to yield a solid. The residue was purified by column chromatography (EtOAc/iso-hexane 7:3) followed by column chromatography (EtOAc) to yield the title compound. Yield: 30 mg.

Workup

  1. stirringstirred for 16 h
  2. customThe solvent was evaporated
  3. additionthe residue diluted in EtOAc (100 ml)
  4. washThis was washed with H2O (3×20 ml) and brine (10 ml)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated
  7. customto yield a solid
  8. customThe residue was purified by column chromatography (EtOAc/iso-hexane 7:3)

Sources & evidence

ORD record
ord-ac0944e4ff8e4c94a18f682cbc350d71
Source dataset
uspto-grants-2012_01
Patent number
US08106063B2

Reaction notes

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