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

HRID 57886Notes

Reaction equation

HRID 57886 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:23]=[N:22][CH:21]=[C:20]([CH3:24])[N:19]=4)[N:14]=[CH:13][C:12]=3[CH:11]=[N:10]2)=[N:6][C:7]=1F.[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.CN1CCOCC1.O>CN1CCCC1=O>[Cl:1][C:2]1[C:7]([N:25]2[CH2:30][CH2:29][CH2:28][C@H:27]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:36])([CH3:35])[CH3:37])[CH2:26]2)=[N:6][C:5]([N:9]2[C:17]3[CH:16]=[C:15]([C:18]4[CH:23]=[N:22][CH:21]=[C:20]([CH3:24])[N:19]=4)[N:14]=[CH:13][C:12]=3[CH:11]=[N:10]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 1514171tert-butyl N-[(3S)-piperidin-3-yl]carbamateHCID 867070791-(5-Chloro-6-fluoro-2-pyridyl)-6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridine

Product 1

HCID 86707081tert-butyl N-[(3S)-1-[3-chloro-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3-piperidyl]carbamateYield 69%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 1-(5-chloro-6-fluoro-2-pyridyl)-6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridine; (0.6372 mmol; 217.1 mg), tert-butyl N-[(3S)-3-piperidyl]carbamate (1.912 mmol; 382.9 mg), and N-Methylmorpholine (3.186 mmol; 326 mg; 0.354 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, then purified on silica eluted with 0 to 6% MeOH in DCM to afford tert-butyl N-[(3S)-1-[3-chloro-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3-piperidyl]carbamate (229.4 mg, 69%).

Workup

  1. filtrationThe precipitate was collect by filtration
  2. custompurified on silica
  3. washeluted with 0 to 6% MeOH in DCM

Sources & evidence

ORD record
ord-390daa0e0a4d4fc4a8326db6e27e2ccb
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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