tert-butyl N-[(3S)-piperidin-3-yl]carbamate → (S)-tert-butyl (1-(6-(6-(6-ethylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperidin-3-yl)carbamate

HRID 57857Notes

Reaction equation

[CH2:1]([C:3]1[N:8]=[C:7]([C:9]2[N:14]=[CH:13][C:12]3[CH:15]=[N:16][N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20](F)[N:19]=4)[C:11]=3[CH:10]=2)[CH:6]=[N:5][CH:4]=1)[CH3:2].[NH:25]1[CH2:30][CH2:29][CH2:28][C@H:27]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:26]1>CS(C)=O>[C:34]([O:33][C:32](=[O:38])[NH:31][C@H:27]1[CH2:28][CH2:29][CH2:30][N:25]([C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([N:17]3[C:11]4[CH:10]=[C:9]([C:7]5[CH:6]=[N:5][CH:4]=[C:3]([CH2:1][CH3:2])[N:8]=5)[N:14]=[CH:13][C:12]=4[CH:15]=[N:16]3)[N:19]=2)[CH2:26]1)([CH3:37])([CH3:35])[CH3:36]

Participants

Conditions

Temperature: 95 °C

Procedure

A solution containing 6-(6-ethylpyrazin-2-yl)-1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridine (75 mg, 0.23 mmol) and tert-butyl N-[(3S)-3-piperidyl]carbamate (234 mg, 1.17 mmol) in methyl sulfoxide 2.0 mL was heated 95° C. The reaction was quenched with water then extracted with EtOAc. The organic layers was dried with sodium sulfate, filtered, and concentrated in vacuum. The crude product was purified by flash chromatography (EtOAc/Heptane eluted at 65% EtOAc) to give (S)-tert-butyl(1-(6-(6-(6-ethylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperidin-3-yl)carbamate (80 mg) in 68% yield.

Workup

customThe reaction was quenched with water
extractionthen extracted with EtOAc
dry with materialThe organic layers was dried with sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuum
customThe crude product was purified by flash chromatography (EtOAc/Heptane eluted at 65% EtOAc)

Sources & evidence

ORD record: ord-38545b2f4f1d488abaff1c72f5829b38
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434725B2

Reaction notes

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