Pyridine → HCID 57393827, compound

HRID 2076123Notes

Reaction equation

HRID 2076123 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH3:14][O:15][C:16]1[CH:24]=[C:23]([NH:25][C:26]2[S:27][C:28]3[CH2:34][CH2:33][CH2:32][CH:31]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:29]=3[N:30]=2)[CH:22]=[CH:21][C:17]=1[C:18]([NH2:20])=O.N1C=CC=CC=1>O1CCOCC1>[CH3:14][O:15][C:16]1[CH:24]=[C:23]([NH:25][C:26]2[S:27][C:28]3[CH2:34][CH2:33][CH2:32][CH:31]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:29]=3[N:30]=2)[CH:22]=[CH:21][C:17]=1[C:18]#[N:20]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 9845Trifluoroacetic anhydride2×HCID 86632609HCID 86632609, compound

Product 1

HCID 57393827HCID 57393827, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Trifluoroacetic acid anhydride (257 uL, 1.83 mmol) was added slowly to a cooled suspension of 2-methoxy-4-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-ylamino)-benzamide (625 mg, 1.65 mmol) in dioxane (2 mL) and pyridine (292 uL, 3.6 mmol). The white suspension was stirred for 30 minutes under cooling and then for 2 hours at 50° C. and for 3 hours at 80° C. Additional trifluoroacetic acid anhydride (300 uL), pyridine (400 uL) and dioxane (5 mL) were added and the reaction was stirred at 80° C. for 2 hours resulting in a clear brown solution. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic layer was washed twice with saturated aqueous sodium hydrogen carbonate, brine, dried over magnesium sulfate, filtered and the solvent was removed under reduced pressure. The residue was purified on silica gel using dichloromethane with 4% methanol as eluent to yield the title compound (236 mg, 40%) as a beige foam. MS ISP (m/e): 362.3 (100) [(M+H)+].

Workup

  1. temperatureunder cooling
  2. waitfor 2 hours at 50° C.
  3. waitfor 3 hours at 80° C
  4. stirringthe reaction was stirred at 80° C. for 2 hours
  5. customresulting in a clear brown solution
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was partitioned between ethyl acetate and water
  8. washThe organic layer was washed twice with saturated aqueous sodium hydrogen carbonate, brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customthe solvent was removed under reduced pressure
  12. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-9b405e2020af4d038b3468f28da6bce9
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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