Hydrochloric Acid → (S)-4,5-Dimethyl-3-(3-methylpiperazin-1-yl)-6-phenylpyridazine

HRID 2093360Notes

Reaction equation

HRID 2093360 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[N:4][C:3]=1[N:15]1[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[C@@H:17]([CH3:28])[CH2:16]1.Cl.O1CCOCC1>CO>[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:5]=[N:4][C:3]=1[N:15]1[CH2:20][CH2:19][NH:18][C@@H:17]([CH3:28])[CH2:16]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 58359248(S)-tert-Butyl 4-(4,5-dimethyl-6-phenylpyridazin-3-yl)-2-methylpiperazine-1-carboxylate

Product 1

HCID 58359255(S)-4,5-Dimethyl-3-(3-methylpiperazin-1-yl)-6-phenylpyridazineYield 95.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Treat a solution of (S)-tert-butyl 4-(4,5-dimethyl-6-phenylpyridazin-3-yl)-2-methylpiperazine-1-carboxylate (2.93 g, 7.66 mmol) in MeOH (20 mL) with 4 M HCl in 1,4-dioxane (10 mL, 40.0 mmol). Stir the reaction mixture at ambient temperature overnight. Concentrate the reaction mixture under reduced pressure. Dissolve the residue in MeOH, and pour onto an SCX column (Varian, 10 g). Rinse the column with MeOH. Elute the desired product with 2M NH3/MeOH. Concentrate under reduced pressure to afford the title compound (2.07 g, 95%). ES/MS m/z 283.0 (M+1).

Workup

  1. concentrationConcentrate the reaction mixture under reduced pressure
  2. dissolutionDissolve the residue in MeOH
  3. additionpour onto an SCX column (Varian, 10 g)
  4. washRinse the column with MeOH
  5. washElute the desired product with 2M NH3/MeOH
  6. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-ee5469865a50457f97c64a2025638dc5
Source dataset
uspto-grants-2013_05
Patent number
US08445493B2

Reaction notes

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