Sodium Bicarbonate → 4-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]butyl acetate

HRID 1926057Notes

Reaction equation

HRID 1926057 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:17]2[C:16](Cl)=[N:15][CH:14]=[N:13][C:12]=2[CH:11]=[CH:10]1)(=[O:3])[CH3:2].[Cl:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][C:26]=1[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=1)[NH2:23].C(=O)([O-])O.[Na+]>C(O)(C)C>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:17]2[C:16]([NH:23][C:22]3[CH:24]=[CH:25][C:26]([O:27][C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:35])([F:36])[F:37])[CH:29]=4)=[C:20]([Cl:19])[CH:21]=3)=[N:15][CH:14]=[N:13][C:12]=2[CH:11]=[CH:10]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 196269843-Chloro-4-[3-(trifluoromethyl)phenoxy]anilineHCID 866157664-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)butyl acetate

Product 1

HCID 675212554-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]butyl acetateYield 50.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)butyl acetate (302 mg) in isopropyl alcohol (2.24 mL) was added 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline (421 mg), and the mixture was stirred in an oil bath at a temperature of 100° C. for 3.5 hrs. The reaction mixture was allowed to cool to room temperature, 5% aqueous sodium hydrogen carbonate solution (35 mL) was added, and the mixture was extracted with ethyl acetate (50 mL×3). The organic layer was washed successively with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to basic silica gel chromatography (eluent:hexane/ethyl acetate=95/5→20/80). The object fraction was concentrated under reduced pressure and dried to give the title compound (293 mg) as a white powder.

Workup

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with ethyl acetate (50 mL×3)
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. concentrationThe object fraction was concentrated under reduced pressure
  7. customdried

Sources & evidence

ORD record
ord-1eb5a20d68404a98acea15d6a5c44020
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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