Pyridine → Piperidin-3-yl(methyl)carbamate

HRID 1923907ノート

反応式

HRID 1923907 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:7](Cl)(=O)C(C)C.[C:13](=[O:23])([O:15]CC1CCCNC1)[NH2:14].[Li+].[OH-]>CN1C(=O)CCC1.CC#N.O.C(Cl)Cl.O>[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([O:15][C:13](=[O:23])[NH:14][CH3:7])[CH2:2]1

参加物

9

反応物 4

HCID 1049PyridineHCID 3939Lithium HydroxideHCID 62325Isobutyryl chlorideHCID 19082825HCID 19082825、化合物

生成物 1

HCID 81908379Piperidin-3-yl(methyl)carbamate収率 51%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 13387N-methyl-2-pyrrolidone溶媒HCID 18373917Acetonitrile--water (1/1)溶媒

実験手順

Pyridine (1 mL) and isobutyryl chloride (0.421 g, 3.95 mmol) were added to (R)-tert-butyl 1-(3-amino-5-chloro-1H-pyrrolo [2, 3-1)]pyridin-4-yl)piperidin-3-yl(methyl) carbamate (0.300 g, 0.790 mmol; Example 112, Step A) in NMP (2 mL), and the reaction was stirred at room temperature for 1 hour. 3M aqueous LiOH (3 mL) was then added, and the reaction was stirred for 10 minutes. Water (10 mL) and DCM (10 mL) were then added, and the organic layer was separated, dried, filtered and concentrated. The crude residue was purified by reverse phase chromatography (Biotage SP4, C-18 12M+, 5-95% CH3CN/water) to give (R)-tert-butyl 1-(5-chloro-3-isobutyramido-1H-pyrrolo[2, 3-1)]pyridin-4-yl)piperidin-3-yl(methyl)carbamate (0.180 g, 51% yield).

後処理

  1. stirringthe reaction was stirred for 10 minutes
  2. customthe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by reverse phase chromatography (Biotage SP4

出典と根拠

ORDレコード
ord-296de4787fce440da8f6a6539a793ec3
出典データセット
uspto-grants-2012_05
特許番号
US08178131B2

反応ノート

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