Triethylamine → HCID 86726825, compound

HRID 1499607Notes

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.[CH:14]1([C@H:17]2[CH2:22][NH:21][CH2:20][C@@H:19]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C@@H:18]2[OH:31])[CH2:16][CH2:15]1.C(N(CC)CC)C>C(O)(C)C>[CH:14]1([C@H:17]2[CH2:22][N:21]([C:2]3[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]4[CH2:11][CH2:12][CH2:13][C:3]=34)[CH2:20][C@@H:19]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[C@@H:18]2[OH:31])[CH2:15][CH2:16]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-chloro-3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridine (0.094 g, 0.47 mmol), tert-butyl [(3R,4R,5S)-5-cyclopropyl-4-hydroxypiperidin-3-yl]carbamate (0.13 g, 0.51 mmol), and triethylamine (0.26 mL, 1.9 mmol) in isopropyl alcohol (2 mL) was heated at 90° C. for 2 days. The desired product partially precipitated from the reaction mixture and was collected by filtration, washed with hexanes and dried under reduced pressure to afford pure sub-title compound (0.080 g). The filtrate was concentrated under reduced pressure and purified by flash column chromatography (20 g silica gel column, eluting with 0-15% MeOH/DCM) to afford further sub-title compound (0.034 g, total 0.114 g, 58%). LCMS (ESI) m/z calc. for C21H31N4O5 419.2 [M+H]+. found 419.1.

Workup

customThe desired product partially precipitated from the reaction mixture
filtrationwas collected by filtration
washwashed with hexanes
customdried under reduced pressure

Sources & evidence

ORD record: ord-1e649eadc3d8426ca58d0134b631562a
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09200004B2

Reaction notes

Loading…