Pyridine → HCID 23111588, compound

HRID 1816949Notes

Reaction equation

HRID 1816949 reaction equation
Cl[C:2]([O:4][C:5]1C=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][CH:6]=1)=O.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:27]3[N:28]=[C:29]([NH2:31])[N:30]=[C:26]3[N:25]=[CH:24][CH:23]=2)=[CH:18][CH:17]=1.N1C=CC=CC=1.[OH-].[Na+].CN1[C:45](=[O:46])N(C)CC1>>[CH3:2][O:4][CH2:5][CH2:6][CH2:7][CH:8]([NH:11][C:45]([NH:31][C:29]1[N:30]=[C:26]2[N:25]=[CH:24][CH:23]=[C:22]([C:19]3[CH:18]=[CH:17][C:16]([O:15][CH3:14])=[CH:21][CH:20]=3)[N:27]2[N:28]=1)=[O:46])[CH3:9]

Participants

6

Reactant 5

HCID 1049PyridineHCID 66611,3-Dimethyl-2-imidazolidinoneHCID 14798Sodium HydroxideHCID 821294-Nitrophenyl chloroformateHCID 2767333SBB052101

Product 1

HCID 23111588HCID 23111588, compound

Procedure

4-nitrophenyl chloroformate (644 mg) was dissolved in DMI (26 ml). Thereafter, while stirring under cooling on ice, 7-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylamine (the compound obtained in Reference Example 8; 514 mg) and pyridine (347 μl) were added to the solution. The obtained mixture was stirred for 40 minutes under cooling on ice. Thereafter, 4-methoxy-1-methylpropylamine (500 mg) was added thereto, and the obtained mixture was stirred for 1 hour under cooling on ice. Subsequently, the reaction solution was stirred at a room temperature overnight. Thereafter, an ice block and an aqueous 3 M sodium hydroxide solution were added to the reaction solution, followed by extraction with methylene chloride. The organic layer was washed with a saturated saline solution and then dried over anhydrous sodium sulfate. The solvent was then distilled off under a reduced pressure. The obtained residual solution was further subjected to vacuum distillation to eliminate DMI. Thereafter, the distillation residue was dissolved in ethyl acetate (100 ml), and the organic layer was washed with 1 M hydrochloric acid (30 ml×4) and then dried over anhydrous sodium sulfate. The solvent was distilled off under a reduced pressure. The obtained residue was purified by silica gel column chromatography (eluted with 0% to 20% methanol-containing ethyl acetate) to obtain the captioned compound (242 mg).

Workup

  1. customobtained in Reference Example 8
  2. stirringThe obtained mixture was stirred for 40 minutes
  3. temperatureunder cooling on ice
  4. stirringthe obtained mixture was stirred for 1 hour
  5. temperatureunder cooling on ice
  6. stirringSubsequently, the reaction solution was stirred at a room temperature overnight
  7. extractionfollowed by extraction with methylene chloride
  8. washThe organic layer was washed with a saturated saline solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThe solvent was then distilled off under a reduced pressure
  11. distillationThe obtained residual solution was further subjected to vacuum distillation
  12. dissolutionThereafter, the distillation residue was dissolved in ethyl acetate (100 ml)
  13. washthe organic layer was washed with 1 M hydrochloric acid (30 ml×4)
  14. dry with materialdried over anhydrous sodium sulfate
  15. distillationThe solvent was distilled off under a reduced pressure
  16. customThe obtained residue was purified by silica gel column chromatography (eluted with 0% to 20% methanol-containing ethyl acetate)

Sources & evidence

ORD record
ord-c4f18ec2ef264b498f4a1228552ac2de
Source dataset
uspto-grants-2009_10
Patent number
US07598244B2

Reaction notes

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