Sodium Bicarbonate → HCID 57597243, compound

HRID 1925966Notes

Reaction equation

HRID 1925966 reaction equation
C([O:9][CH2:10]/[CH:11]=[CH:12]/[C:13]1[N:21]([CH3:22])[C:20]2[C:19](OC3C=CC=CC=3)=[N:18][CH:17]=[N:16][C:15]=2[CH:14]=1)(=O)C1C=CC=CC=1.[Cl:30][C:31]1[CH:32]=[C:33]([CH:35]=[CH:36][C:37]=1[O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[CH:41]=1)[NH2:34].Cl.N1C=CC=CC=1.C(=O)([O-])O.[Na+]>CN1CCCC1=O>[Cl:30][C:31]1[CH:32]=[C:33]([NH:34][C:19]2[C:20]3[N:21]([CH3:22])[C:13](/[CH:12]=[CH:11]/[CH2:10][OH:9])=[CH:14][C:15]=3[N:16]=[CH:17][N:18]=2)[CH:35]=[CH:36][C:37]=1[O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[CH:41]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 70592633-Chloro-4-(3-fluorobenzyloxy)anilineHCID 10176127Pyridinium chlorideHCID 67520970HCID 67520970, compound

Product 1

HCID 57597243HCID 57597243, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of (2E)-3-(5-methyl-4-phenoxy-5H-pyrrolo[3,2-d]pyrimidin-6-yl)-2-propenyl benzoate (100 mg), 3-chloro-4-[(3-fluorobenzyl)oxy]aniline (130 mg), pyridine hydrochloride (36 mg) and 1-methyl-2-pyrrolidone (0.518 mL) was stirred with heating at 140° C. for 4 hrs. After cooling to room temperature, aqueous sodium hydrogen carbonate (20 mL) was added to the reaction mixture and the mixture was extracted with ethyl acetate (100 mL). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (0.518 mL)/ethanol (0.518 mL), 1N aqueous sodium hydroxide solution (0.518 mL) was added, and the mixture was stirred at room temperature for 2 hrs. Tetrahydrofuran/ethyl acetate (1:1, 50 mL) and saturated brine (30 mL) were added, and the mixture was extracted. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by basic silica gel column chromatography (eluent, ethyl acetate:methanol=100:0→85:15) to give the title compound (45 mg) as crystals.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with ethyl acetate (100 mL)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in tetrahydrofuran (0.518 mL)/ethanol (0.518 mL), 1N aqueous sodium hydroxide solution (0.518 mL)
  6. additionwas added
  7. stirringthe mixture was stirred at room temperature for 2 hrs
  8. additionTetrahydrofuran/ethyl acetate (1:1, 50 mL) and saturated brine (30 mL) were added
  9. extractionthe mixture was extracted
  10. dry with materialThe organic layer was dried over magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was separated
  13. custompurified by basic silica gel column chromatography (eluent, ethyl acetate:methanol=100:0→85:15)

Sources & evidence

ORD record
ord-7184f9c53f1840359c77328f1e74514b
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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