Diisopropylethylamine → N-[(4-aminophenyl)methyl]pyridine-2-carboxamide

HRID 2234368

Reaction equation

HRID 2234368 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([O-:9])=O.[NH2:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[NH2:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH:16][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[O:9])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4278144-AminobenzylamineHCID 6920223PicolinateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 60891447N-[(4-aminophenyl)methyl]pyridine-2-carboxamideYield 68.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Pyridine-2-carboxylate (Aldrich; 0.35 g, 2.84 mmol), 4-aminobenzylamine (Aldrich; 0.51 g, 4.26 mmol) and HATU (1.65 g, 4.26 mmol) were dissolved in DMF (7.5 ml). N,N-Diisopropylethylamine (1.5 ml, 8.53 mmol) was added and the mixture stirred at room temperature for 2 h. The mixture was absorbed on to an SCX column, washed with methanol and eluted with ammonia in methanol. Product containing fractions were concentrated and the residue purified by normal phase chromatography (2% MeOH/DCM) to give a yellow solid (440 mg). which was suspended in DCM/Et2O and filtered to give the title compound as a pale yellow solid (235 mg, 36%).

Workup

  1. customThe mixture was absorbed on to an SCX column
  2. washwashed with methanol
  3. washeluted with ammonia in methanol
  4. additionProduct containing fractions
  5. concentrationwere concentrated
  6. customthe residue purified by normal phase chromatography (2% MeOH/DCM)

Sources & evidence

ORD record
ord-5ced0b6da781499e8cfaad59ac1a9933
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Linked notes

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