HCID 86646068, compound → HCID 86646067, compound

HRID 1800667Notes

Reaction equation

HRID 1800667 reaction equation
[CH3:1][N:2]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:22](=[O:33])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)[CH:16]=1)[C:3]1[N:8]=[C:7]([S:9][C:10]#[N:11])[C:6]([N+:12]([O-])=O)=[CH:5][N:4]=1>C(O)(=O)C>[NH2:11][C:10]1[S:9][C:7]2[N:8]=[C:3]([N:2]([CH3:1])[C:15]3[CH:16]=[C:17]([NH:21][C:22](=[O:33])[C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:31])([F:30])[F:32])[CH:24]=4)[CH:18]=[CH:19][CH:20]=3)[N:4]=[CH:5][C:6]=2[N:12]=1

Participants

3

Reactant 1

HCID 86646068HCID 86646068, compound

Product 1

HCID 86646067HCID 86646067, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-[methyl(3-{[3-(trifluoromethyl)benzoyl]amino}phenyl)amino]-5-nitropyrimidin-4-yl thiocyanate (1.79 g, 3.76 mmol) in acetic acid (100 mL) was added reduced iron (5.50 g, 98.5 mmol), and the mixture was stirred with heating at 100° C. for 1.5 hr. The reaction solution was allowed to cool to room temperature, and the insoluble material was filtered off and the residue was washed with acetic acid. The combined filtrate and washing solution were concentrated under reduced pressure, and the residue was diluted with tetrahydrofuran (50 mL) and ethyl acetate (250 mL). This liquid was washed with saturated aqueous sodium hydrogen carbonate solution (150 mL), saturated aqueous ammonium chloride solution (150 mL) and saturated brine (150 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate/methanol=100/0→90/10) and recrystallized from ethyl acetate and tetrahydrofuran to give N-{3-[(2-amino[1,3]thiazolo[5,4-d]pyrimidin-5-yl)(methyl)amino]phenyl}-3-(trifluoromethyl)benzamide (compound of Example D1) (424 mg, 26%) as colorless crystals.

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe insoluble material was filtered off
  3. washthe residue was washed with acetic acid
  4. washThe combined filtrate and washing solution
  5. concentrationwere concentrated under reduced pressure
  6. additionthe residue was diluted with tetrahydrofuran (50 mL) and ethyl acetate (250 mL)
  7. washThis liquid was washed with saturated aqueous sodium hydrogen carbonate solution (150 mL), saturated aqueous ammonium chloride solution (150 mL) and saturated brine (150 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationThe insoluble material was filtered off
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe residue was purified by basic silica gel column chromatography (ethyl acetate/methanol=100/0→90/10)
  12. customrecrystallized from ethyl acetate and tetrahydrofuran

Sources & evidence

ORD record
ord-56f3fa9e2752443fb088985cfcfd3a19
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

Loading…