6-(3-(Pyrrolidin-1-yl)prop-1-ynyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine → 6-(3-(Pyrrolidin-1-yl)propyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

HRID 1615462Notes

Reaction equation

HRID 1615462 reaction equation
[N:1]1([CH2:6][C:7]#[C:8][C:9]2[CH:10]=[C:11]3[N:16]([CH:17]=2)[N:15]=[CH:14][N:13]=[C:12]3[NH2:18])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>[Pd].CO>[N:1]1([CH2:6][CH2:7][CH2:8][C:9]2[CH:10]=[C:11]3[N:16]([CH:17]=2)[N:15]=[CH:14][N:13]=[C:12]3[NH2:18])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 706652016-(3-(Pyrrolidin-1-yl)prop-1-ynyl)pyrrolo[2,1-f][1,2,4]triazin-4-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 666017846-(3-(Pyrrolidin-1-yl)propyl)pyrrolo[2,1-f][1,2,4]triazin-4-amineYield 91.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a round-bottom flask, the compound (269 mg, 1.14 mmol) prepared in Example 11, palladium/carbon (10%, 20 mg) and methanol (10 mL) was added and the atmosphere was replaced with hydrogen gas at 1 atm. After 18 hours, the mixture was filtered through celite and the celite pad was washed with methanol. The methanol was removed in vacuo to obtain the title compound (257 mg) having the following physical data.

Workup

  1. filtrationthe mixture was filtered through celite
  2. washthe celite pad was washed with methanol
  3. customThe methanol was removed in vacuo

Sources & evidence

ORD record
ord-a86885829d8b4346a7ed282ac13f5d9d
Source dataset
uspto-grants-2014_07
Patent number
US08765754B2

Reaction notes

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