Pyridine → HCID 12096564, compound

HRID 2083926Notes

Reaction equation

HRID 2083926 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][C:15]3[C:16]([NH2:21])=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.N1C=CC=CC=1.[CH3:28][O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1>C(Cl)(Cl)Cl>[CH3:28][O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([NH:21][C:16]2[C:15]([NH:14][CH2:13][CH:10]3[CH2:11][CH2:12][N:7]([C:4]4[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=4)[CH2:8][CH2:9]3)=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:35])=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7477p-Anisoyl chlorideHCID 12150698N1-[1-(4-pyridyl)piperidin-4-ylmethyl)-1,2-benzenediamine

Product 1

HCID 12096564HCID 12096564, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of N1-[1-(4-pyridyl)piperidin-4-ylmethyl]-1,2-benzenediamine (212 mg, 0.75 mmol) and pyridine (4 mL) in chloroform (2 mL) at 0° C. was treated with a solution of 4-methoxybenzoyl chloride (128 mg, 0.75 mmol) in chloroform. The mixture was allowed to warm to roam temperature and stir for 17 h. The mixture was concentrated and the residue was dissolved in EtOAc. The organic layer was washed with 1 N NaOH (2×), water (3×), brine (1×), dried (K2CO3), and concentrated. The residue was purified by RPHPLC, yielding 52 mg (17%) of the title compound as a hydrochloride salt.

Workup

  1. temperatureto warm
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue was dissolved in EtOAc
  4. washThe organic layer was washed with 1 N NaOH (2×), water (3×), brine (1×)
  5. dry with materialdried (K2CO3)
  6. concentrationconcentrated
  7. customThe residue was purified by RPHPLC

Sources & evidence

ORD record
ord-595d5fd6eeae4882b8e1cf8cd001f372
Source dataset
uspto-grants-2004_04
Patent number
US06716839B2

Reaction notes

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