Sodium Hydroxide → HCID 44556233, compound

HRID 221997Notes

Reaction equation

HRID 221997 reaction equation
FC(F)(F)C([NH:5][C:6]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[C:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:27][C:26]4[C:25]5=[N:35][N:36]=[C:37]([C:38]6[N:43]=[CH:42][CH:41]=[CH:40][N:39]=6)[N:24]5[CH:23]=[CH:22][C:21]=4[N:20]=3)=[CH:15][CH:14]=2)[CH2:9][C:8]([OH:12])([CH2:10][OH:11])[CH2:7]1)=O.[OH-].[Na+]>CCO>[NH2:5][C:6]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[C:28]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)=[CH:27][C:26]4[C:25]5=[N:35][N:36]=[C:37]([C:38]6[N:43]=[CH:42][CH:41]=[CH:40][N:39]=6)[N:24]5[CH:23]=[CH:22][C:21]=4[N:20]=3)=[CH:15][CH:14]=2)[CH2:9][C:8]([CH2:10][OH:11])([OH:12])[CH2:7]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58229874HCID 58229874, compound

Product 1

HCID 44556233HCID 44556233, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2,2,2-trifluoro-N-(3-hydroxy-3-(hydroxymethyl)-1-{4-[9-phenyl-3-(2-primidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutyl)acetamide (4-14) (5 mg, 0.009 mmol) in EtOH (6 mL) was added NaOH (5M in water, 0.5 mL, 0.50 mmol), and the mixture was refluxed for 3 hours. The solvent was removed under reduced pressure, and the residue was purified by preparative TLC eluting with 5% MeOH in CHCl3 to give 3-amino1-(hydroxymethyl)-3-{4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutanol (4-15) as a white solid. HRMS (M+H)+: observed=516.2148, calculated=516.2147.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by preparative TLC
  4. washeluting with 5% MeOH in CHCl3

Sources & evidence

ORD record
ord-034d06444cb444bf9e6372fb801e51c8
Source dataset
uspto-grants-2012_06
Patent number
US08207169B2

Reaction notes

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