Trifluoroacetic acid → (S)-2-(1-Aminoethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052347Notes

Reaction equation

HRID 1052347 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9](=[O:11])[N:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:7]([C@@H:18]([NH:20]C(=O)OC(C)(C)C)[CH3:19])=[N:6]2.FC(F)(F)C(O)=O>ClCCl>[NH2:20][C@H:18]([C:7]1[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9](=[O:11])[C:10]2=[C:2]([CH3:1])[CH:3]=[CH:4][N:5]2[N:6]=1)[CH3:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131736112(S)-tert-Butyl (1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)carbamate

Product 1

HCID 90102580(S)-2-(1-Aminoethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 79.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl (1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)carbamate (950 mg, 2.58 mmol) was dissolved in 5 mL dichloromethane and trifluoroacetic acid (993 μl, 12.89 mmol) was added. The mixture was stirred at room temperature overnight. The reaction mixture was evaporated to dryness and was partitioned between ethyl acetate and potassium bicarbonate. The organic layer was washed with water, brine and dried over sodium sulphate, filtered and concentrated under reduced pressure to give 0.55 g (78% yield) of the title compound that was used in the next step without any further purification. Purity 97%.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customwas partitioned between ethyl acetate and potassium bicarbonate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b7f55ca3c3784704afa418d9ca6d4029
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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