Pyridine → Piperidin-3-yl(methyl)carbamate

HRID 1923907노트

반응식

HRID 1923907 반응식
[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

참가 물질

9

반응물 4

HCID 1049PyridineHCID 3939Lithium HydroxideHCID 62325Isobutyryl chlorideHCID 19082825HCID 19082825, 화합물

생성물 1

HCID 81908379Piperidin-3-yl(methyl)carbamate수율 51%

시약·촉매·용매 4

HCID 962Water용매HCID 6344Dichloromethane용매HCID 13387N-methyl-2-pyrrolidone용매HCID 18373917Acetonitrile--water (1/1)용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-296de4787fce440da8f6a6539a793ec3
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178131B2

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