Hydrochloric Acid → HCID 86697001, compound

HRID 2279261Notes

Reaction equation

HRID 2279261 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., 2 H), 6.92 (s, 1 H), 4.15 (s, 2 H), 4.00 (s, 3 H), 2.58 (s, 3 H).

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-0876ac9195884412b70cd154b83205b0
Source dataset
uspto-grants-2015_09
Patent number
US09133215B2

Reaction notes

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