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

HRID 2093360ノート

反応式

HRID 2093360 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ee5469865a50457f97c64a2025638dc5
出典データセット
uspto-grants-2013_05
特許番号
US08445493B2

反応ノート

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