2-Pyridinemethanamine → 2-chloro-5-phenyl-N-(pyridin-2-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

HRID 2170143Notes

Reaction equation

HRID 2170143 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]2=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:10]=[CH:11][N:4]2[N:3]=1.CCN(C(C)C)C(C)C.[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH2:33][NH2:34]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:34][CH2:33][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][N:27]=2)[C:5]2=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:10]=[CH:11][N:4]2[N:3]=1

Participants

5

Reactant 3

HCID 195092-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 90386287HCID 90386287, compound

Product 1

HCID 903861572-chloro-5-phenyl-N-(pyridin-2-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amineYield 35.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,4-Dichloro-5-phenylpyrrolo[2,1-f][1,2,4]triazine (0.560 g, 2.12 mmol) was dissolved in THF (15 mL) and then DIPEA (1.85 mL, 10.6 mmol) was added followed by the addition of pyridin-2-ylmethanamine (0.688 g, 6.36 mmol). Then the reaction mixture was stirred at room temperature for 14 h. The reaction mixture was concentrated under reduced pressure to remove THF and to this residue water (10 mL) added. The aqueous solution was extracted with CH2Cl2 (25×3 mL) and the organic layer was separated, dried over anhydrous sodium sulfate and was concentrated under reduced pressure. The residue was purified by column chromatography using CombiFlash (REDISEP®, silica gel, 40 g, 20% EtOAc/hexanes) to afford 2-chloro-5-phenyl-N-(pyridin-2-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (0.250 g, 35.1%). LCMS Condition B-39: retention time 2.10 min, [M+1]=336.0.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto remove THF
  3. additionto this residue water (10 mL) added
  4. extractionThe aqueous solution was extracted with CH2Cl2 (25×3 mL)
  5. customthe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationwas concentrated under reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-0de4bc4a1da84fa1aa146a372bd8e36a
Source dataset
uspto-grants-2015_06
Patent number
US09050345B2

Reaction notes

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