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

HRID 57940Notes

Reaction equation

[F:1][CH:2]([F:26])[C:3]1[CH:4]=[CH:5][C:6]([N:10]2[C:18]3[CH:17]=[C:16]([C:19]4[CH:24]=[N:23][CH:22]=[C:21]([CH3:25])[N:20]=4)[N:15]=[CH:14][C:13]=3[CH:12]=[N:11]2)=[N:7][C:8]=1F.[NH:27]1[CH2:32][CH2:31][CH2:30][C@H:29]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:28]1.CN1CCOCC1.O>CN1CCCC1=O>[F:26][CH:2]([F:1])[C:3]1[C:8]([N:27]2[CH2:32][CH2:31][CH2:30][C@H:29]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:38])([CH3:37])[CH3:39])[CH2:28]2)=[N:7][C:6]([N:10]2[C:18]3[CH:17]=[C:16]([C:19]4[CH:24]=[N:23][CH:22]=[C:21]([CH3:25])[N:20]=4)[N:15]=[CH:14][C:13]=3[CH:12]=[N:11]2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-[5-(difluoromethyl)-6-fluoro-2-pyridyl]-6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridine (0.0977 mmol; 34.8 mg), tert-butyl N-[(3S)-3-piperidyl]carbamate (0.147 mmol; 29.3 mg), and N-Methylmorpholine (0.244 mmol; 24.9 mg; 0.0271 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, and extracted with EtOAc. The organic layer was concentrated. The residue was purified on silica eluted with 0 to 100% EtOAc in DCM to afford tert-butyl N-[(3S)-1-[3-(difluoromethyl)-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3-piperidyl]carbamate (˜52.4 mg, 100%).

Workup

extractionextracted with EtOAc
concentrationThe organic layer was concentrated
customThe residue was purified on silica
washeluted with 0 to 100% EtOAc in DCM

Sources & evidence

ORD record: ord-c71c912d670e47f98984725baba885b5
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434725B2

Reaction notes

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