Potassium Carbonate → HCID 9848569, compound

HRID 1647819Notes

Reaction equation

HRID 1647819 reaction equation
I[CH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14][S:15]([NH:18][CH3:19])(=[O:17])=[O:16])[CH:12]=2)[NH:7][CH:6]=1.[CH3:20][O:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][C:27]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:20][O:21][C:22]1[C:27]([N:28]2[CH2:29][CH2:30][N:31]([CH2:2][CH2:3][CH2:4][C:5]3[C:13]4[C:8](=[CH:9][CH:10]=[C:11]([CH2:14][S:15]([NH:18][CH3:19])(=[O:17])=[O:16])[CH:12]=4)[NH:7][CH:6]=3)[CH2:32][CH2:33]2)=[CH:26][CH:25]=[N:24][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15288307HCID 15288307, compoundHCID 152883081-(3-Methoxypyridin-4-yl)piperazine

Product 1

HCID 9848569HCID 9848569, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-(3-iodopropyl)-N-methyl-1H-indole-5-methanesulfonamide (0.556 g, 1.26 mmol), 1-(3-methoxy-4-pyridinyl)piperazine (0.4 g, 2.02 mmol), and K2CO3 (0.5 g, 3.6 mmol) in 30 mL of MeCN was heated to reflux for 12 h. The reaction mixture was cooled, concentrated in vacuo, and the residue dissolved EtOAc. The EtOAc solution was washed with water, dried (MgSO4), filtered and concentrated in vacuo. Silica gel chromatography (100:3:1 CH2Cl2 -MeOH-Et3N) of the residue gave 4-(5-methoxy-4-pyridinyl)-1-[3-[5-[[(methylamino)sulfonyl]methyl]-1-H-indol-3-yl]propyl]piperazine (300 mg, 52%). The hydrochloride salt was prepared by dissolving the free base in 3 equivalents of 1.5 M HCl in EtOH. The solution was concentrated in vacuo and the residue recrystallized from MeOH to yield the title compound (380 mg, 50%): mp 100°-103° C. Anal. Calcd for C23H31N5O3S.3.8 HCl: C, 46.34; H, 5.88; N, 11.78. Found: C, 46.32; H, 6.18; N, 11.67

Workup

  1. temperatureto reflux for 12 h
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated in vacuo
  4. dissolutionthe residue dissolved EtOAc
  5. washThe EtOAc solution was washed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-839b7e769c8b4ddb8a3891a816b25e30
Source dataset
uspto-grants-1995_07
Patent number
US05434154

Reaction notes

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