HCID 86716226, compound → HCID 86716225, compound

HRID 512198Notes

Reaction equation

HRID 512198 reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][N:20]=[N:19][CH:18]=2)[CH2:8][NH:9]C(=O)OC(C)(C)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][N:20]=[N:19][CH:18]=2)[CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 86716226HCID 86716226, compound

Product 1

HCID 86716225HCID 86716225, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl (2-phenyl-2-(pyridazin-4-yl)ethyl)carbamate (120 mg, 0.40 mmol) in DCM (2 ml) and TFA(2 ml) was stirred at room temperature for 4 hours. The solvent was removed under reduced pressure and the residue was diluted with sat.aq Na2CO3 to adjust pH=9-10, then, extracted with AcOEt (3×30 ml), the combined organic layer was washed with brine, dried over Na2SO4 and concentrated to get the 2-phenyl-2-(pyridazin-4-yl)ethanamine(crude 80 mg), which was used for next step directly.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with sat.aq Na2CO3
  3. extractionextracted with AcOEt (3×30 ml)
  4. washthe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9dad5b742e29449db3bae03daa44e16b
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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