Potassium Carbonate → HCID 58486430, compound

HRID 1890758Notes

Reaction equation

HRID 1890758 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[C:6]([CH3:9])[C:7]=1[CH3:8].[CH3:11][N:12]([CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.O>[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:23]2[CH2:22][CH2:21][CH:20]([N:12]([CH3:11])[C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:25][CH2:24]2)=[C:6]([CH3:9])[C:7]=1[CH3:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27568064-N-Boc-4-N-Methyl-aminopiperidineHCID 211875053,6-Dichloro-4,5-dimethylpyridazine

Product 1

HCID 58486430HCID 58486430, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Heat a mixture of 3,6-dichloro-4,5-dimethylpyridazine (11.0 g, 62.1 mmol), tert-butyl methyl(piperidin-4-yl)carbamate (23.3 g, 109 mmol), and powdered K2CO3 (17.2 g, 124 mmol) in DMSO (310 mL) at 120° C. for 2 d. Cool the reaction mixture, dilute with H2O, and filter off the solid. Rinse the solid with H2O, and dry under vacuum at 45° C. Dissolve the solid in CH2Cl2, and pass the solution through a pad of silica gel, eluting with CH2Cl2. Concentrate the organic layer under reduced pressure to obtain the title compound as a yellow solid (14.3 g, 65%). ES/MS m/z (35Cl) 355.0 (M+1).

Workup

  1. temperatureHeat
  2. temperatureCool the reaction mixture
  3. filtrationfilter off the solid
  4. washRinse the solid with H2O
  5. customdry under vacuum at 45° C
  6. dissolutionDissolve the solid in CH2Cl2
  7. washeluting with CH2Cl2
  8. concentrationConcentrate the organic layer under reduced pressure

Sources & evidence

ORD record
ord-0e280228bf874837b5fb25def8fb9b0b
Source dataset
uspto-grants-2013_08
Patent number
US08507490B2

Reaction notes

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