N,N-Diethylethylenediamine → 5-Amino-pyridine-2-carboxylic acid (2-diethylamino-ethyl)-amide

HRID 1921748Notes

Reaction equation

HRID 1921748 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.[CH2:11]([N:13]([CH2:17][CH3:18])[CH2:14][CH2:15][NH2:16])[CH3:12].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CCN(C(C)C)C(C)C>C1COCC1>[CH2:11]([N:13]([CH2:17][CH3:18])[CH2:14][CH2:15][NH:16][C:8]([C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[CH:7][N:6]=1)=[O:10])[CH3:12]

Participants

6

Reactant 4

HCID 60993N,N-DiethylethylenediamineHCID 81531DiisopropylethylamineHCID 41797265-Aminopyridine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 590231165-Amino-pyridine-2-carboxylic acid (2-diethylamino-ethyl)-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 5-amino-pyridine-2-carboxylic acid is coupled to N,N-diethyl-ethane-1,2-diamine (0.47 mL, 3.32 mmol), in the presence of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.26 g, 3.33 mmol), and DIPEA (0.59 mL, 3.33 mmol) in THF (10 mL). The mixture is stirred at room temperature for 48 hours. The solvent is removed in vacuo and the residue partitioned between water-EtOAc. The organic layer is dried over MgSO4, filtered and concentrated to give a residue purified by silica gel column chromatography. 5-Amino-pyridine-2-carboxylic acid (2-diethylamino-ethyl)-amide is isolated (394 mg, 100%) eluting with 96:4 DCM:NH3 (7M in MeOH).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue partitioned between water-EtOAc
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-8e87e8095790424abad7751f4ae2efd4
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Reaction notes

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