Hydrochloric Acid → HCID 86697001, compound

HRID 1191315Notes

Reaction equation

HRID 1191315 reaction equation
Br[C:2]1[C:3]([CH2:9][N:10](C)[C:11](=O)OC(C)(C)C)=[N:4][S:5][C:6]=1[O:7][CH3:8].CC([O-])=O.[K+].Cl.O1CCOCC1>CO.CCOC(C)=O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:8][O:7][C:6]1[S:5][N:4]=[C:3]([CH2:9][NH:10][CH3:11])[CH:2]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 517044Potassium AcetateHCID 86697002HCID 86697002, compound

Product 1

HCID 86697001HCID 86697001, compoundYield 122.7%

Reagents, catalysts & solvents 3

HCID 178418851HCID 178418851, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a sealed 20 ml microwave vial, a solution of compound 52 (340 mg, 1.01 mmol), KOAc (297 mg, 3.02 mmol) and Pd(PtBu3)2 (52.7 mg, 0.101 mmol) in MeOH (5 mL) was heated in the microwave for 45 min at 100° C. Diluted with EtOAc, washed with water and brine, dried (MgSO4), filtered and concentrated under vacuum. The residue was dissolved in DCM (2.50 mL) then 4 N HCl in dioxane (2.52 mL, 10.1 mmol) was added. The reaction was stirred at room temperature and concentrated under vacuum to give compound 178 (196 mg, quantitative) as a solid. 1H NMR (400 MHz, DMSO-d6) δ 9.46 (br. s., 2H), 6.92 (s, 1H), 4.15 (s, 2H), 4.00 (s, 3H), 2.58 (s, 3H).

Workup

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. dissolutionThe residue was dissolved in DCM (2.50 mL)
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0717d1e6d73f441ca66fc9ee4e64b99f
Source dataset
uspto-grants-2014_03
Patent number
US08680111B2

Reaction notes

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