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

HRID 57830Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[C:17]3[CH:16]=[C:15]([C:18]4[CH:19]=[N:20][CH:21]=[C:22]([CH2:24][CH3:25])[CH:23]=4)[N:14]=[CH:13][C:12]=3[CH:11]=[N:10]2)=[N:6][C:7]=1F.[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.O>CN1CCCC1=O>[Cl:1][C:2]1[C:7]([N:26]2[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]2)=[N:6][C:5]([N:9]2[C:17]3[CH:16]=[C:15]([C:18]4[CH:19]=[N:20][CH:21]=[C:22]([CH2:24][CH3:25])[CH:23]=4)[N:14]=[CH:13][C:12]=3[CH:11]=[N:10]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-(5-chloro-6-fluoro-2-pyridyl)-6-(5-ethyl-3-pyridyl)pyrazolo[4,3-c]pyridine (0.155 mmol; 54.9 mg), tert-butyl N-[(3S)-3-piperidyl]carbamate (0.466 mmol; 93.2 mg), and N-Methylmorpholine (1.55 mmol; 159 mg; 0.172 mL) in 1-Methyl-2-pyrrolidinone (3 mL) in a sealed pressure vial was heated at 100° C. overnight. The mixture was poured into water. The precipitate was collect by filtration and dried on high vacuum to afford tert-butyl N-[(3S)-1-[3-chloro-6-[6-(5-ethyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3-piperidyl]carbamate (66.6 mg, 80%), which was used without further purification.

Workup

filtrationThe precipitate was collect by filtration
customdried on high vacuum

Sources & evidence

ORD record: ord-c3af1278fdc04597a28aec2a1ad06f27
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434725B2

Reaction notes

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