4-Methylmorpholine → tert-butyl N-[(3S)-1-[6-[6-(5-isopropyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3-piperidyl]carbamate

HRID 57815Notes

Reaction equation

F[C:2]1[N:7]=[C:6]([N:8]2[C:16]3[CH:15]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[C:21]([CH:23]([CH3:25])[CH3:24])[CH:22]=4)[N:13]=[CH:12][C:11]=3[CH:10]=[N:9]2)[CH:5]=[CH:4][CH:3]=1.[NH:26]1[CH2:31][CH2:30][CH2:29][C@H:28]([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:27]1.CN1CCOCC1>CN1CCCC1=O>[CH:23]([C:21]1[CH:22]=[C:17]([C:14]2[N:13]=[CH:12][C:11]3[CH:10]=[N:9][N:8]([C:6]4[N:7]=[C:2]([N:26]5[CH2:31][CH2:30][CH2:29][C@H:28]([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:37])([CH3:36])[CH3:38])[CH2:27]5)[CH:3]=[CH:4][CH:5]=4)[C:16]=3[CH:15]=2)[CH:18]=[N:19][CH:20]=1)([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 1-(6-fluoro-2-pyridyl)-6-(5-isopropyl-3-pyridyl)pyrazolo[4,3-c]pyridine (0.3032 mmol; 120.0 mg), tert-butyl N-[(3S)-3-piperidyl]carbamate (0.9095 mmol; 182.2 mg), and N-methylmorpholine (3.032 mmol; 310 mg; 0.337 mL) in 1-Methyl-2-pyrrolidinone (3 mL) in a sealed pressure vial was heated at 120° C. overnight. The mixture was cooled to room temperature, and then partitioned between EtOAc and water. The organic layer was concentrated to afford tert-butyl N-[(3S)-1-[6-[6-(5-isopropyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3-piperidyl]carbamate, which was used without purification.

Workup

temperatureThe mixture was cooled to room temperature
custompartitioned between EtOAc and water
concentrationThe organic layer was concentrated

Sources & evidence

ORD record: ord-35cbf45eae8e46b6ab238812161ab596
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434725B2

Reaction notes

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