(3R)-3-Aminopiperidine, 3-BOC protected → HCID 67045415, compound

HRID 1923965Notes

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.F[C:16]1[C:21]([O:22][CH2:23][CH2:24][O:25][CH3:26])=[CH:20][N:19]=[C:18]2[NH:27][CH:28]=[C:29]([NH:30][C:31]([CH:33]3[CH2:35][CH2:34]3)=[O:32])[C:17]=12>C(O)(CC)C>[CH:33]1([C:31]([NH:30][C:29]2[C:17]3[C:18](=[N:19][CH:20]=[C:21]([O:22][CH2:23][CH2:24][O:25][CH3:26])[C:16]=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:27][CH:28]=2)=[O:32])[CH2:34][CH2:35]1

Participants

Conditions

Temperature: 150 °C

Procedure

(R)-tert-Butyl piperidin-3-ylcarbamate (307 mg, 1.53 mmol) was added to N-(4-fluoro-5-(2-methoxyethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)cyclopropanecarboxamide (150 mg, 0.511 mmol) in s-BuOH (3 mL), and the reaction was stirred at 150° C. for 24 hours in a sealed tube. After cooling down and concentration, the residue was purified by reverse phase chromatography (SP4, 25M, water/ACN 90/10->0/100, 30 CV) to yield (R)-tert-butyl 1-(3-(cyclopropanecarboxamido)-5-(2-methoxyethoxy)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate (113 mg, 46.7% yield) as a solid.

Workup

temperatureAfter cooling down
concentrationconcentration
customthe residue was purified by reverse phase chromatography (SP4, 25M, water/ACN 90/10->0/100, 30 CV)

Sources & evidence

ORD record: ord-9cbd085daa0a429e9e6488d10579b3a7
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178131B2

Reaction notes

Loading…