Triethylamine → N-(4-Methoxyphenyl)-2-[1-(4-pyridyl)piperidin-4-ylmethyl]aminopyridine-3-carboxamide

HRID 397545Notes

Reaction equation

HRID 397545 reaction equation
Cl[C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[N:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][CH:28]([CH2:31][NH2:32])[CH2:27][CH2:26]2)=[CH:21][CH:20]=1.C(N(CC)CC)C>C(O)C>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([NH:10][C:8]([C:7]2[C:2]([NH:32][CH2:31][CH:28]3[CH2:27][CH2:26][N:25]([C:22]4[CH:23]=[CH:24][N:19]=[CH:20][CH:21]=4)[CH2:30][CH2:29]3)=[N:3][CH:4]=[CH:5][CH:6]=2)=[O:9])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8403012-Chloro-N-(4-methoxyphenyl)-3-pyridinecarboxamideHCID 10607746[1-(Pyridin-4-yl)piperidin-4-yl]methanamine

Product 1

HCID 9844870N-(4-Methoxyphenyl)-2-[1-(4-pyridyl)piperidin-4-ylmethyl]aminopyridine-3-carboxamideYield 24%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A pressure tube (Aldrich) was charged with 2-chloro-N-(4-methoxyphenyl)pyridine-3-carboxamide (139 mg, 0.524 mmol), 1-(4-pyridyl)piperidine-4-methylamine (100 mg, 0.524 mmol), triethylamine (0.22 mL), and ethanol (3 mL). The mixture was placed in a 110° C. bath for 5 days. The mixture was concentrated and the residue purified by RPHPLC, yielding 52 mg (24%) of the title compound as a hydrochloride salt.

Workup

  1. customwas placed in a 110° C.
  2. customfor 5 days
  3. concentrationThe mixture was concentrated
  4. customthe residue purified by RPHPLC

Sources & evidence

ORD record
ord-c51a011a72a6402ca59cd831ad5d7b3b
Source dataset
uspto-grants-2003_08
Patent number
US06610704B1

Reaction notes

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