Triethylamine → tert-Butyl [(3S)-1-(3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)piperidin-3-yl]carbamate

HRID 924402Notes

Reaction equation

Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]2[CH2:11][CH2:12][CH2:13][C:3]=12.[NH:14]1[CH2:19][CH2:18][CH2:17][C@H:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:15]1.C(N(CC)CC)C>C(O)(C)C>[N+:8]([C:7]1[C:2]([N:14]2[CH2:19][CH2:18][CH2:17][C@H:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[CH2:15]2)=[C:3]2[CH2:13][CH2:12][CH2:11][C:4]2=[N:5][CH:6]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-chloro-3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridine (40.0 mg, 0.201 mmol), tert-butyl (3S)-piperidin-3-ylcarbamate (80.7 mg, 0.403 mmol) and triethylamine (84.2 μL, 0.604 mmol) in isopropyl alcohol (0.462 mL) was stirred at 100° C. for 30 min. The mixture was concentrated and purified by flash chromatography on a silica gel column (12 g column, 0-40% EtOAc in hexanes) to give the sub-title compound as light yellow powder (43 mg, 59%). LCMS calc. for C18H27N4O4 (M+H)+: m/z=363.3. Found: 363.2.

Workup

concentrationThe mixture was concentrated
custompurified by flash chromatography on a silica gel column (12 g column, 0-40% EtOAc in hexanes)

Sources & evidence

ORD record: ord-0813734ead4b40d59d45626d2c535df2
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278950B2

Reaction notes

Loading…