Hydrochloric Acid → 5-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]pentan-1-ol

HRID 1926067Notes

Reaction equation

HRID 1926067 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:18]2[C:17](Cl)=[N:16][CH:15]=[N:14][C:13]=2[CH:12]=[CH:11]1)(=O)C.[Cl:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][C:27]=1[O:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=1)[NH2:24].[OH-].[Na+].Cl>C(O)(C)C>[Cl:20][C:21]1[CH:22]=[C:23]([NH:24][C:17]2[C:18]3[N:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][OH:4])[CH:11]=[CH:12][C:13]=3[N:14]=[CH:15][N:16]=2)[CH:25]=[CH:26][C:27]=1[O:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:37])([F:38])[F:36])[CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 196269843-Chloro-4-[3-(trifluoromethyl)phenoxy]anilineHCID 568508045-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)pentyl acetate

Product 1

HCID 568508065-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]pentan-1-olYield 78.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 5-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)pentyl acetate (200 mg) and 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline (265 mg) in isopropyl alcohol (3.5 mL) was stirred at 80° C. for 14 hrs. 1N Aqueous sodium hydroxide solution (2.1 mL) was added at 0° C., and the mixture was stirred at room temperature for 1 hr. 1N Hydrochloric acid (2.0 mL) was added to the reaction system, and the mixture was extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogen carbonate and saturated brine and dried over magnesium sulfate. After concentration under reduced pressure, the residue was separated and purified by silica gel column chromatography (eluent, ethyl acetate→ethyl acetate:methanol=1:19) to give a colorless solid. Recrystallization from ethyl acetate-hexane gave the title compound (275 mg) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with aqueous sodium hydrogen carbonate and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. customthe residue was separated
  6. custompurified by silica gel column chromatography (eluent, ethyl acetate→ethyl acetate:methanol=1:19)
  7. customto give a colorless solid
  8. customRecrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-ad4b5372a2c2443d8dd122e6ae364afb
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

Loading…