Formaldehyde → 1-[(4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)methyl]pyrrolidin-3-ol

HRID 578757Notes

Reaction equation

HRID 578757 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.[CH2:7]=O.[N:9]1[N:10]2[CH:18]=[CH:17][CH:16]=[C:11]2[C:12]([NH2:15])=[N:13][CH:14]=1>C(O)(=O)C>[NH2:15][C:12]1[C:11]2=[CH:16][CH:17]=[C:18]([CH2:7][N:1]3[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]3)[N:10]2[N:9]=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 982104-HydroxypyrrolidineHCID 10441749Pyrrolo[2,1-f][1,2,4]triazin-4-amine

Product 1

HCID 903891581-[(4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)methyl]pyrrolidin-3-ol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

3-Pyrrolidinol (1.56 g, 17.9 mmol) and 37% formalin solution (1.45 g, 17.9 mmol) were dissolved in acetic acid (75 mL) and stirred at room temperature for 10 min. To this solution was added a solution of pyrrolo[2,1-f][1,2,4]triazin-4-amine (2.0 g, 14.9 mmol) in acetic acid (75 mL), and the mixture was stirred at 60° C. for 4 h. After evaporation, the residue was taken up in 200 mL of 1 N aqueous potassium carbonate solution and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative HPLC (method 4) to give 390 mg (11% of th.) of the title compound.

Workup

  1. stirringthe mixture was stirred at 60° C. for 4 h
  2. customAfter evaporation
  3. extractionextracted with ethyl acetate (3×200 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by preparative HPLC (method 4)

Sources & evidence

ORD record
ord-8d3bb599ecce4a5ea8e7598b1ec2a864
Source dataset
uspto-grants-2015_05
Patent number
US09040691B2

Reaction notes

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