2-(Aminomethyl)aniline → HCID 67411378, compound

HRID 909159Notes

Reaction equation

HRID 909159 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH2:11])[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:12](C1NC=CN=1)(C1NC=CN=1)=[O:13].[NH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH2:32]>ClCCCl>[NH2:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][NH:24][C:12]([NH:11][C:7]1[N:8]([CH3:10])[N:9]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1)=[O:13]

Participants

5

Reactant 3

HCID 1780962-(Aminomethyl)anilineHCID 27352873-tert-Butyl-1-methyl-1H-pyrazol-5-amineHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 67411378HCID 67411378, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

5-tert-Butyl-2-methyl-2H-pyrazol-3-ylamine (10s) (4.8 g, 31 mmol) and carbonyl diimidazole (4.6 g, 32 mmol) were partially dissolved in DCE (100 mL) and heated at 70° C. for 2 hours. The reaction was cooled and 2-aminomethyl-phenylamine (9s) (4.2 g, 34 mmol) was added and the reaction was stirred 14 hours. The reaction was concentrated to remove the solvent and then partitioned between EtOAc and 0.5N HCl (60 mL). The organic phase was washed with NH4Cl and water and dried (MgSO4). The solution was concentrated and recrystallized from EtOAc (200 mL) to provide the desired product (5s) (4.6 g, 49% yield).

Workup

  1. temperatureThe reaction was cooled
  2. concentrationThe reaction was concentrated
  3. customto remove the solvent
  4. custompartitioned between EtOAc and 0.5N HCl (60 mL)
  5. washThe organic phase was washed with NH4Cl and water
  6. dry with materialdried (MgSO4)
  7. concentrationThe solution was concentrated
  8. customrecrystallized from EtOAc (200 mL)

Sources & evidence

ORD record
ord-965ab5e38d2443d18e0e0d3b8b422c20
Source dataset
uspto-grants-2011_09
Patent number
US08017641B2

Reaction notes

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