Hydrochloric Acid → HCID 178527452, compound

HRID 631866Notes

Reaction equation

HRID 631866 reaction equation
C([Sn](Cl)(CCCC)CCCC)CCC.[N-:15]=[N+:16]=[N-:17].[Na+].[C:19]([C:21]1[C:30]2[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=2[CH:24]=[CH:23][C:22]=1[NH:31][S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:34])=[O:33])#[N:20].Cl>CN(C=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[NH:15]1[C:19]([C:21]2[C:30]3[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=3[CH:24]=[CH:23][C:22]=2[NH:31][S:32]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)(=[O:34])=[O:33])=[N:20][N:17]=[N:16]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 15096Tributyltin ChlorideHCID 33557Sodium AzideHCID 68296403HCID 68296403, compound2×

Product 1

HCID 178527452HCID 178527452, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
220 °C

Procedure

Tri-n-butyl tin chloride (0.16 mL) was added to a solution of sodium azide (0.039 g) in DMF (0.6 mL) and the mixture was stirred for 5 minutes. Tetra-butyl ammonium bromide (0.0065 g) was then added, followed by N-(1-cyano-5,6,7,8-tetrahydronaphthalen-2-yl)benzenesulfonamide (Intermediate 1, 0.177 g). The mixture was heated by microwave irradiation at 220° C. for 1 hour. The solution was then acidified with 1N hydrochloric acid and the products were extracted into DCM, dried with magnesium sulfate and filtered. The filtrate was evaporated to dryness and the residue was purified by preparative HPLC (C18). The fractions containing the desired product were combined, and the solvent was removed by evaporation to give the title compound as a beige solid (0.01 g).

Workup

  1. extractionthe products were extracted into DCM
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by preparative HPLC (C18)
  6. additionThe fractions containing the desired product
  7. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-c9e28d41af594154b24334a6db0551f5
Source dataset
uspto-grants-2016_04
Patent number
US09321740B2

Reaction notes

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