(3R)-3-Aminopiperidine, 3-BOC protected → HCID 67045387, compound

HRID 408245Notes

Reaction equation

HRID 408245 reaction equation
[Br:1][C:2]1[C:3](F)=[C:4]2[C:10]([NH:11][C:12](=[O:20])[C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[NH:22]1[CH2:27][CH2:26][CH2:25][C@@H:24]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:23]1.CC#N.O>CCCCO>[Br:1][C:2]1[C:3]([N:22]2[CH2:27][CH2:26][CH2:25][C@@H:24]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:32])[CH3:34])[CH2:23]2)=[C:4]2[C:10]([NH:11][C:12](=[O:20])[C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1514172(3R)-3-Aminopiperidine, 3-BOC protectedHCID 18373917Acetonitrile--water (1/1)HCID 60205398HCID 60205398, compound

Product 1

HCID 67045387HCID 67045387, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
155 °C

Procedure

N-(5-Bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-3-fluorobenzamide (306 mg, 0.869 mmol) and (R)-tert-butyl piperidin-3-ylcarbamate (522 mg, 2.61 mmol) were placed in n-BuOH (5 mL) and heated to 155° C. for 42 hours in a sealed tube. The reaction was cooled to room temperature and concentrated to dryness. The crude residue was purified by C-18 reverse phase flash chromatography (Biotage Horizon unit, C-18 25M column, 5-80% CH3CN/water gradient) to give (R)-tert-butyl 1-(5-bromo-3-(3-fluorobenzamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate (125 mg, 27% yield).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated to dryness
  3. customThe crude residue was purified by C-18 reverse phase flash chromatography (Biotage Horizon unit

Sources & evidence

ORD record
ord-8af1ef402d2b4df6a47f26ce7df456c7
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

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