Water → HCID 86707111, compound

HRID 57922Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]2[C:16]3[CH:15]=[C:14]([C:17]4[CH:22]=[N:21][CH:20]=[C:19]([CH3:23])[N:18]=4)[N:13]=[CH:12][C:11]=3[CH:10]=[N:9]2)[CH:5]=[CH:4][C:3]=1[C:24]([F:27])([F:26])[F:25].[NH:28]1[CH2:33][CH2:32][CH2:31][C@H:30]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:29]1.CN1CCOCC1.O>CN1CCCC1=O>[CH3:23][C:19]1[N:18]=[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:28]5[CH2:33][CH2:32][CH2:31][C@H:30]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:39])([CH3:38])[CH3:40])[CH2:29]5)[C:3]([C:24]([F:27])([F:26])[F:25])=[CH:4][CH:5]=4)[C:16]=3[CH:15]=2)[CH:22]=[N:21][CH:20]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 1-[6-chloro-5-(trifluoromethyl)-2-pyridyl]-6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridine (0.0876 mmol; 59.7 mg), tert-butyl N-[(3S)-3-piperidyl]carbamate (0.263 mmol; 52.6 mg), and N-Methylmorpholine (0.263 mmol; 26.9 mg; 0.0292 mL) in 1-methyl-2-pyrrolidinone (3 mL) in a sealed pressure vial was heated at 120° 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 Heptane to afford tert-butyl N-[(3S)-1-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-3-(trifluoromethyl)-2-pyridyl]-3-piperidyl]carbamate as a white solid (37.0 mg, 65%).

Workup

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

Sources & evidence

ORD record: ord-8a184df263034253b2114af3613ad03b
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434725B2

Reaction notes

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