Sodium Hydroxide → 3-Methyl-1-{4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutanamine

HRID 221996Notes

Reaction equation

HRID 221996 reaction equation
FC(F)(F)C([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][CH:8]([CH3:10])[CH2:7]1)=O.[OH-].[Na+]>CCO.C(Cl)(Cl)Cl>[CH3:10][CH:8]1[CH2:7][C:6]([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)([NH2:5])[CH2:9]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 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

Product 1

HCID 445561343-Methyl-1-{4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutanamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 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) (3.3 mg, 0.006 mmol) and NaOH (5M in water, 0.30 mL) in EtOH (3 mL) was stirred at 70° C. for 15 hours. The mixture was diluted with CHCl3, washed with water and brine, dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified by preparative TLC eluting with 10% MeOH in CHCl3 to give 3-methyl-1-{-4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutanamine (4-13) as a white form. HRMS (M+H)+: observed=484.2250, calculated=484.2243.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by preparative TLC
  6. washeluting with 10% MeOH in CHCl3

Sources & evidence

ORD record
ord-533e8974613045a5bcd1fb00a1638fe1
Source dataset
uspto-grants-2012_06
Patent number
US08207169B2

Reaction notes

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