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

HRID 2093360노트

반응식

HRID 2093360 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ee5469865a50457f97c64a2025638dc5
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445493B2

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