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Hydrochloric Acid → 3-(4-Benzyl-2-methylpiperazin-1-yl)-6-(4-fluorophenyl)-4,5-dimethylpyridazine

HRID 2093365
ノート
印刷プレビュー

反応式

HRID 2093365 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]=[N:16][C:17]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[C:18]([CH3:21])[C:19]=2[CH3:20])[CH:10]([CH3:29])[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.Cl>C1COCC1.O1CCOCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]=[N:16][C:17]([C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)=[C:18]([CH3:21])[C:19]=2[CH3:20])[CH:10]([CH3:29])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 583592571-Benzyl-4-(6-(4-fluorophenyl)-4,5-dimethylpyridazin-3-yl)-3-methylpiperazin-2-one

生成物 1

HCID 583592493-(4-Benzyl-2-methylpiperazin-1-yl)-6-(4-fluorophenyl)-4,5-dimethylpyridazine

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒
HCID 31275
1,4-Dioxane
溶媒

反応条件

温度
50 °C

実験手順

Treat a solution of 1-benzyl-4-(6-(4-fluorophenyl)-4,5-dimethylpyridazin-3-yl)-3-methylpiperazin-2-one (2.84 g, 7.02 mmol) in THF (70 mL) with borane-methyl sulfide complex (1.96 mL, 21.1 mmol). Heat the resulting mixture at 50° C. for 2 h. Cool the reaction mixture in an ice bath, add MeOH (20 mL) via a dropping funnel followed by 4 M HCl in 1,4-dioxane (20 mL). Heat the resulting mixture at 65° C. for 1 h. Concentrate the mixture under reduced pressure. Partition the residue between CH2Cl2 and saturated NaHCO3 (aq). Separate the layers, and extract the aqueous layer with CH2Cl2. Combine the organic layers, dry over Na2SO4, filter, and concentrate under reduced pressure. Purify the residue by flash silica gel chromatography (gradient of 0 to 3% 2 M NH3/MeOH in CH2Cl2) to afford the title compound as a waxy solid (2.45 g, 89%). ES/MS m/z 391.2 (M+1).

後処理

  1. temperatureCool the reaction mixture in an ice bath
  2. temperatureHeat the resulting mixture at 65° C. for 1 h
  3. concentrationConcentrate the mixture under reduced pressure
  4. customPartition the residue between CH2Cl2 and saturated NaHCO3 (aq)
  5. customSeparate the layers
  6. extractionextract the aqueous layer with CH2Cl2
  7. dry with materialdry over Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate under reduced pressure
  10. customPurify the residue by flash silica gel chromatography (gradient of 0 to 3% 2 M NH3/MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-4a51965c934f4e61a13d58129d79af43
出典データセット
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08445493B2

反応ノート

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