(3R)-3-Aminopiperidine, 3-BOC protected → (R)-tert-butyl 1-(3-(cyclopropanecarboxamido)-5-ethoxy-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate

HRID 408396Notes

Reaction equation

HRID 408396 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:2]1.[CH2:15]([O:17][C:18]1[C:19](F)=[C:20]2[C:26]([NH:27][C:28]([CH:30]3[CH2:32][CH2:31]3)=[O:29])=[CH:25][NH:24][C:21]2=[N:22][CH:23]=1)[CH3:16]>C(O)CCC>[CH:30]1([C:28]([NH:27][C:26]2[C:20]3[C:21](=[N:22][CH:23]=[C:18]([O:17][CH2:15][CH3:16])[C:19]=3[N:1]3[CH2:6][CH2:5][CH2:4][C@@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:2]3)[NH:24][CH:25]=2)=[O:29])[CH2:31][CH2:32]1

Participants

4

Reactant 2

HCID 1514172(3R)-3-Aminopiperidine, 3-BOC protectedHCID 60205640N-(5-ethoxy-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)cyclopropanecarboxamide

Product 1

HCID 67045564(R)-tert-butyl 1-(3-(cyclopropanecarboxamido)-5-ethoxy-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamateYield 25.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
160 °C

Procedure

(R)-tert-Butyl piperidin-3-ylcarbamate (205 mg, 1.0 mmol) was added to N-(5-ethoxy-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)cyclopropanecarboxamide (90 mg, 0.34 mmol) in n-butanol (2 mL). The reaction was stirred at 160° C. for 24 hours in a sealed tube. After cooling down and concentration, the residue was purified by reverse phase chromatography (Biotage SP4, C-18 25M+, water/ACN 90/10→10190, 30CV) to yield (R)-tert-butyl 1-(3-(cyclopropanecarboxamido)-5-ethoxy-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate (39 mg) as a solid.

Workup

  1. temperatureAfter cooling down
  2. concentrationconcentration
  3. customthe residue was purified by reverse phase chromatography (Biotage SP4

Sources & evidence

ORD record
ord-17ede4a996244df0a492c0d182d45441
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

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