Diisopropylethylamine → HCID 67045537, compound

HRID 875841Notes

Reaction equation

HRID 875841 reaction equation
[Br:1][C:2]1[C:3](F)=[C:4]2[C:10]([NH:11][C:12](=[O:15])[CH2:13][OH:14])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[NH:17]1[CH2:22][CH2:21][CH2:20][C@@H:19]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:18]1.CCN(C(C)C)C(C)C.CC#N.O>CCCCO>[Br:1][C:2]1[C:3]([N:17]2[CH2:22][CH2:21][CH2:20][C@@H:19]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH2:18]2)=[C:4]2[C:10]([NH:11][C:12](=[O:15])[CH2:13][OH:14])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1514172(3R)-3-Aminopiperidine, 3-BOC protectedHCID 18373917Acetonitrile--water (1/1)HCID 60205571HCID 60205571, compound

Product 1

HCID 67045537HCID 67045537, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
140 °C

Procedure

N-(5-Bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-hydroxyacetamide (0.200 g, 0.694 mmol), (R)-tert-butyl piperidin-3-ylcarbamate (0.417 g, 2.08 mmol), and DIEA (0.363 mL, 2.08 mmol) were placed in n-BuOH (2 mL) and heated to 140° C. for 18 hours. The reaction was then cooled to room temperature and concentrated to dryness. The resulting residue was purified by reverse phase chromatography (Biotage SP4, C-18 25M+, 5-75 CH3CN/water) to give (R)-tert-butyl 1-(5-bromo-3-(2-hydroxyacetamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate (0.220 g, 68% yield).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. concentrationconcentrated to dryness
  3. customThe resulting residue was purified by reverse phase chromatography (Biotage SP4

Sources & evidence

ORD record
ord-46bb1d5f12764110ac9d2bbee20784df
Source dataset
uspto-grants-2015_03
Patent number
US08981085B2

Reaction notes

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