HCID 86679692, compound → 1403249-01-3

HRID 1507096Notes

Reaction equation

HRID 1507096 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([NH:11]CC2C=CC(OC)=CC=2)[CH:8]=[N:9][CH:10]=1)[CH3:3]>C(O)(C(F)(F)F)=O>[CH3:3][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([NH2:11])[CH:8]=[N:9][CH:10]=1)[CH3:1]

Participants

3

Reactant 1

HCID 86679692HCID 86679692, compound

Product 1

HCID 682226921403249-01-3Yield 52%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

5-((dimethylamino)methyl)-N-(4-methoxybenzyl)pyridin-3-amine (LVI) (0.15 g, 0.56 mmol) was dissolved in TFA (2.0 mL) and stirred at room temperature for 1 h. The TFA was removed, and the residue was treated with 7N ammonia in MeOH/chloroform mixture (7/93) to neutralize the TFA and concentrated again to a residue. The residue was purified by flash silica gel chromatography utilizing a 4 g Thomson normal-phase silica gel cartridge (100% CHCl3→3:97 MeOH[7N NH3]:CHCl3) to afford 5-((dimethylamino)methyl)pyridin-3-amine (LVII) (0.044 g, 0.29 mmol, 52% yield) as a brown oil. ESIMS found for C8H13N3 m/z 152 (M+H).

Workup

  1. customThe TFA was removed
  2. additionthe residue was treated with 7N ammonia in MeOH/chloroform mixture (7/93)
  3. concentrationconcentrated again to a residue
  4. customThe residue was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-f800f687b58440ae8141885c2d414407
Source dataset
uspto-grants-2015_12
Patent number
US09221793B2

Reaction notes

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