HCID 58229857, compound → 2,2,2-trifluoro-N-(3-methyl-1-{-4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutyl)acetamide

HRID 221995Notes

Reaction equation

HRID 221995 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]([NH:5][C:6]1([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:25][C:24]4[C:23]5=[N:33][N:34]=[C:35]([C:36]6[N:41]=[CH:40][CH:39]=[CH:38][N:37]=6)[N:22]5[CH:21]=[CH:20][C:19]=4[N:18]=3)=[CH:13][CH:12]=2)[CH2:9][C:8](=[CH2:10])[CH2:7]1)=[O:4]>[Pd].C1COCC1>[F:43][C:2]([F:1])([F:42])[C:3]([NH:5][C:6]1([C:11]2[CH:12]=[CH:13][C:14]([C:17]3[C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:25][C:24]4[C:23]5=[N:33][N:34]=[C:35]([C:36]6[N:41]=[CH:40][CH:39]=[CH:38][N:37]=6)[N:22]5[CH:21]=[CH:20][C:19]=4[N:18]=3)=[CH:15][CH:16]=2)[CH2:9][CH:8]([CH3:10])[CH2:7]1)=[O:4]

Participants

4

Reactant 1

HCID 58229857HCID 58229857, compound

Product 1

HCID 582298812,2,2-trifluoro-N-(3-methyl-1-{-4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutyl)acetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,2,2-trifluoro-N-(3-methylene-1-{-4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutyl)acetamide (4-11) (5 mg, 0.009 mmol) and palladium on carbon (10%, 10 mg) in THF (5 mL) was stirred under H2 atmosphere at room temperature for 30 minutes. The mixture was filtered through celite pad and the solvent was removed under reduced pressure. The residue was purified by preparative TLC eluting with 5% EtOAc in hexane to give 2,2,2-trifluoro-N-(3-methyl-1-{4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutyl)acetamide (4-12) as a white solid.

Workup

  1. filtrationThe mixture was filtered through celite pad
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified by preparative TLC
  4. washeluting with 5% EtOAc in hexane

Sources & evidence

ORD record
ord-18357d3b49e24d6c967df1b15e2c766f
Source dataset
uspto-grants-2012_06
Patent number
US08207169B2

Reaction notes

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