Trifluoroacetic acid → HCID 9817403, compound

HRID 564758Notes

Reaction equation

HRID 564758 reaction equation
C(OC(=O)[NH:7][C:8]1[C:13]2=[CH:14][S:15][C:16]([NH2:17])=[C:12]2[C:11](=[O:18])[N:10]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[N:9]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C:8]1[C:13]2[C:12](=[C:16]([NH2:17])[S:15][CH:14]=2)[C:11](=[O:18])[N:10]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[N:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 9865102HCID 9865102, compound

Product 1

HCID 9817403HCID 9817403, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [5-amino-3-(4-methoxy-phenyl)-4-oxo-3,4-dihydro-thieno[3,4-d]pyridazin-1-yl]carbamic acid tert-butyl ester (140 mg, 0.36 mmol, prepared as described in example 33) in dichloromethane (20 ml) was added trifluoroacetic acid (5 ml) and the reaction mixture was stirred at room temperature for 1 h. The volatiles were evaporated in vacuo and the residue was dissolved in ethanol and evaporated in vacuo. The semi solid residue was treated with diethyl ether (25 ml) for 16 h, the precipitate was filtered off and dried in vacuo at 50° C. for 16 h affording 30 mg crude title compound. The diethyl ether phase was evaporated and the residue was purified on silica gel (200 ml) using a mixture of ethyl acetate and heptane (3:1) as eluent. Pure fractions were collected and the solvent evaporated in vacuo affording 20 mg (19%) of the title compound as a solid.

Workup

  1. customThe volatiles were evaporated in vacuo
  2. dissolutionthe residue was dissolved in ethanol
  3. customevaporated in vacuo
  4. additionThe semi solid residue was treated with diethyl ether (25 ml) for 16 h
  5. filtrationthe precipitate was filtered off
  6. customdried in vacuo at 50° C. for 16 h
  7. customaffording 30 mg crude title compound
  8. customThe diethyl ether phase was evaporated
  9. customthe residue was purified on silica gel (200 ml)
  10. additiona mixture of ethyl acetate and heptane (3:1) as eluent
  11. customPure fractions were collected
  12. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-7e6dd273f6c54698bfb561232901a99a
Source dataset
uspto-grants-2001_01
Patent number
US06169087A

Reaction notes

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