Potassium Carbonate → HCID 42603358, compound

HRID 2170546Notes

Reaction equation

HRID 2170546 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]([CH3:15])=[C:13]([C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=3)=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Br[CH2:27][CH2:28][O:29]C1CCCCO1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]([CH3:15])=[C:13]([C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:27][CH2:28][OH:29])[CH:20]=3)=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 42603083HCID 42603083, compound

Product 1

HCID 42603358HCID 42603358, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1-[(3,4-dichlorophenyl)methyl]-N-(3-hydroxyphenyl)-5-methyl-1H-1,2,3-triazole-4-carboxamide (Example 31) (0.1 g, 0.29 mmol) in acetonitrile (10 mL) and a couple of drops of DMF, were added 2-[(2-bromoethyl)oxy]tetrahydro-2H-pyran (0.09 μl, 2 eq) and potassium carbonate (0.08 g, 2 eq). The reaction was heated at 40° C. for 1 week. After evaporation, the residue was dissolved in DCM, washed with water and dried over sodium sulphate. After purification by flash chromatography eluting with DCM/MeOH, 98/2, the crude compound was dissolved in MeOH and some drops of a concentrated HCl solution in AcOEt were added and the solution was stirred at room temperature for 3 hours. After evaporation, the compound was recrystallised (twice) from methanol and washed with a mixture of ether and pentane. The title compound was obtained as a green solid (45 mg, 36%). HRMS calculated for C19H18Cl2N4O3 (M+H)+ 421.0834. found: 421.0804, Rt: 2.87 min. MP: 144.9° C.

Workup

  1. customAfter evaporation
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with water
  4. dry with materialdried over sodium sulphate
  5. customAfter purification by flash chromatography
  6. washeluting with DCM/MeOH, 98/2
  7. dissolutionthe crude compound was dissolved in MeOH
  8. additionsome drops of a concentrated HCl solution in AcOEt were added
  9. customAfter evaporation
  10. customthe compound was recrystallised (twice) from methanol
  11. washwashed with a mixture of ether and pentane

Sources & evidence

ORD record
ord-a31914386c214fb78891bdac7e2a4987
Source dataset
uspto-grants-2015_06
Patent number
US09051281B2

Reaction notes

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