1-Methylpiperazine → HCID 86700459, compound

HRID 879647Notes

Reaction equation

HRID 879647 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[C:8](I)=[N:9][N:10]([CH3:11])[C:5]2=[CH:4][CH:3]=1.Cl[C:14]1[CH:15]=CC2[C:18](=[C:20](I)[N:21]([CH3:23])N=2)[N:19]=1.CN1CCNCC1.N1CCC[C@H]1C(O)=O>[Cu]I>[Cl:1][C:2]1[N:7]=[C:6]2[C:8]([N:19]3[CH2:14][CH2:15][N:21]([CH3:23])[CH2:20][CH2:18]3)=[N:9][N:10]([CH3:11])[C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 531671-MethylpiperazineHCID 145742L-ProlineHCID 86700460HCID 86700460, compoundHCID 86700461HCID 86700461, compound

Product 1

HCID 86700459HCID 86700459, compound

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
100 °C

Procedure

To a solution of 5-chloro-3-iodo-1-methyl-1H-pyrazolo[4,3-b]pyridine (104 mg, 0.354 mmol, containing the isomer 5-chloro-3-iodo-2-methyl-2H-pyrazolo[4,3-b]pyridine (360 mg, 1.22 mmol) was added 1-methylpiperazine (184 mg, 1.84 mmol), CuI (70 mg, 0.368 mmol), L-proline (84 mg, 0.736 mmol). The reaction mixture was heated at 100° C. for 4 h. The reaction was cooled, washed by sat. NaHCO3, extracted with EtOAc, dried over MgSO4, filtered, concentrated and purified by silica gel column, eluting by 0-100% EtOAc in hexanes to give the product. LCMS-ESI+: calc'd for C12H16ClN5: 266.1 (M+H+); Found: 266.2 (M+H+).

Workup

  1. temperatureThe reaction was cooled
  2. washwashed by sat. NaHCO3
  3. extractionextracted with EtOAc
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel column
  8. washeluting by 0-100% EtOAc in hexanes
  9. customto give the product

Sources & evidence

ORD record
ord-dea244862039419495a0a5aae9001ec3
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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