2-Pyridinemethanamine → HCID 178439828, compound

HRID 1158090Notes

Reaction equation

HRID 1158090 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH2:8].Br[C:10]([CH3:19])([CH:16]([CH3:18])[CH3:17])[C:11]([N:13]=[C:14]=[S:15])=[O:12]>C(Cl)Cl>[CH:16]([C:10]1([CH3:19])[S:15][C:14]([NH:8][CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:13][C:11]1=[O:12])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 195092-PyridinemethanamineHCID 86606009HCID 86606009, compound

Product 1

HCID 178439828HCID 178439828, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridin-2-ylmethanamine (0.22 mL, 2.1 mmol) was added to 2-bromo-2,3-dimethylbutanoyl isothiocyanate (240 mg, 1.1 mmol) at room temperature. The reaction was exothermic, and was stirred at room temperature for 15 min. CH2Cl2 (2 ml) was added, and the resulting precipitate was removed by filtration. The CH2Cl2 solution was concentrated, and the mixture was purified by silica gel column (gradient 1% (10% NH3 in MeOH) to 30% (10% NH3 in MeOH) in CH2Cl2) to give the title compound as an off-white solid (123 mg). Mass Spec.=m/z+ion 264.1 (M+H)

Workup

  1. customthe resulting precipitate was removed by filtration
  2. concentrationThe CH2Cl2 solution was concentrated
  3. customthe mixture was purified by silica gel column (gradient 1% (10% NH3 in MeOH) to 30% (10% NH3 in MeOH) in CH2Cl2)

Sources & evidence

ORD record
ord-58b82ca9912f4f36a6f0f4fd32899b02
Source dataset
uspto-grants-2010_10
Patent number
US07807700B2

Reaction notes

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