Sodium Bicarbonate → HCID 67520944, compound

HRID 1926123Notes

Reaction equation

HRID 1926123 reaction equation
[Cl:1][C:2]1[C:3]2[N:10]([CH2:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17]C3CCCCO3)[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:24][C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][C:31]=1[O:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=1)[NH2:28].C(=O)([O-])O.[Na+]>C(O)(C)C>[ClH:1].[Cl:24][C:25]1[CH:26]=[C:27]([NH:28][C:2]2[C:3]3[N:10]([CH2:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][OH:17])[CH:9]=[CH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:29]=[CH:30][C:31]=1[O:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:41])([F:42])[F:40])[CH:34]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 196269843-Chloro-4-[3-(trifluoromethyl)phenoxy]anilineHCID 86615776HCID 86615776, compound

Product 1

HCID 67520944HCID 67520944, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

4-Chloro-5-{3-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]propyl}-5H-pyrrolo[3,2-d]pyrimidine (380.2 mg) was dissolved in isopropyl alcohol (7 mL), 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline (419.2 mg) was added, and the mixture was stirred at 80° C. for 18 hrs. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=50:50→0:100), and the mixture was dissolved in ethyl acetate (4 mL). 4N Hydrochloric acid-ethyl acetate (0.3 mL) was added to this solution, and the precipitate was collected by filtration, and dried to give the title compound (398.2 mg) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified by silica gel column chromatography (eluent, hexane:ethyl acetate=50:50→0:100)
  7. dissolutionthe mixture was dissolved in ethyl acetate (4 mL)
  8. addition4N Hydrochloric acid-ethyl acetate (0.3 mL) was added to this solution
  9. filtrationthe precipitate was collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-cfc6767dead046c8a0fa91f4c609b6db
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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