N,N'-Dimethylethylenediamine → tert-butyl N-[(3S)-1-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)-2-pyridyl]-2-oxo-3-piperidyl]carbamate

HRID 57932Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([N:8]2[C:16]3[CH:15]=[C:14]([Cl:17])[N:13]=[CH:12][C:11]=3[CH:10]=[N:9]2)[CH:5]=[CH:4][CH:3]=1.[O:18]=[C:19]1[C@@H:24]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:23][CH2:22][CH2:21][NH:20]1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>[Cu]I>[Cl:17][C:14]1[N:13]=[CH:12][C:11]2[CH:10]=[N:9][N:8]([C:6]3[N:7]=[C:2]([N:20]4[CH2:21][CH2:22][CH2:23][C@H:24]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[C:19]4=[O:18])[CH:3]=[CH:4][CH:5]=3)[C:16]=2[CH:15]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A solution containing 1-(6-bromo-2-pyridyl)-6-chloro-pyrazolo[4,3-c]pyridine (200 mg, 0.646 mmol), tert-butyl N-[(3S)-2-oxo-3-piperidyl]carbamate (166 mg, 0.775 mmol), Copper(I) iodide (123 mg, 0.646 mmol), Potassium carbonate (107 mg, 0.775 mmol) and N,N′-Dimethylethylenediamine (114 mg, 1.29 mmol) was stirred at 110° C. 4 h. The reaction was filtered through celite and concentrated. The crude product purified by isco column (EtOAc/Hep eluted at 70% EtOAc) to give the desired product 135 mg 47% yield. MS (ESI) m/z: 443.1.

Workup

custom4 h
filtrationThe reaction was filtered through celite
concentrationconcentrated
customThe crude product purified by isco column (EtOAc/Hep eluted at 70% EtOAc)

Sources & evidence

ORD record: ord-e79c8a0fc3074bbb9cb4c6c5771d3212
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434725B2

Reaction notes

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