Hydrochloric Acid → [3-(3-Chloro-1,2,4-oxadiazol-5-yl)-5-(4-ethylphenyl)piperidin-1-yl](4-hydroxypiperidin-1-yl)-methanone

HRID 661210ノート

反応式

HRID 661210 の反応式
N([O-])=O.[Na+].N[C:6]1[N:10]=[C:9]([CH:11]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH3:24])=[CH:19][CH:18]=3)[CH2:14][N:13]([C:25]([N:27]3[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29][CH2:28]3)=[O:26])[CH2:12]2)[O:8][N:7]=1.[ClH:34]>O>[Cl:34][C:6]1[N:10]=[C:9]([CH:11]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH3:24])=[CH:19][CH:18]=3)[CH2:14][N:13]([C:25]([N:27]3[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29][CH2:28]3)=[O:26])[CH2:12]2)[O:8][N:7]=1

参加物

5

反応物 3

HCID 313Hydrochloric Acid2 回HCID 23668193Sodium NitriteHCID 58116513[3-(3-Amino-1,2,4-oxadiazol-5-yl)-5-(4-ethylphenyl)piperidin-1-yl](4-hydroxypiperidin-1-yl)methanone

生成物 1

HCID 58116548[3-(3-Chloro-1,2,4-oxadiazol-5-yl)-5-(4-ethylphenyl)piperidin-1-yl](4-hydroxypiperidin-1-yl)-methanone

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

A solution of 332 mg (4.81 mmol) of sodium nitrite in 1.25 ml of water was added dropwise at 0° C. to a solution of 1.60 g (2.40 mmol) of the amine from Example 24A in 60% purity in 25 ml of concentrated hydrogen chloride solution. After the addition had ended, the mixture was stirred at 0° C. for 1 h and then at RT for 45 min. The reaction mixture was diluted with 1 N aqueous hydrogen chloride solution and extracted with dichloromethane. The organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by means of preparative HPLC. Yield: 220 mg (22% of theory)

後処理

  1. additionAfter the addition
  2. waitat RT for 45 min
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic phase was dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by means of preparative HPLC

出典と根拠

ORDレコード
ord-a59831364676486ebd72d4820987f90e
出典データセット
uspto-grants-2011_12
特許番号
US08084469B2

反応ノート

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