Pyridine → 3,4-dichloro-N-[1-[6-chloro-4-[(E)-N-hydroxy-C-methylcarbonimidoyl]-2-pyridinyl]piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide

HRID 2233940Notes

Reaction equation

HRID 2233940 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=[C:6]([N:11]2[CH2:16][CH2:15][CH:14]([NH:17][C:18]([C:20]3[NH:21][C:22]([CH3:27])=[C:23]([Cl:26])[C:24]=3[Cl:25])=[O:19])[CH2:13][CH2:12]2)[CH:5]=1)(=O)[CH3:2].N1C=CC=CC=1.Cl.[NH2:35][OH:36]>CCO>[Cl:25][C:24]1[C:23]([Cl:26])=[C:22]([CH3:27])[NH:21][C:20]=1[C:18]([NH:17][CH:14]1[CH2:15][CH2:16][N:11]([C:6]2[CH:5]=[C:4](/[C:1](=[N:35]/[OH:36])/[CH3:2])[CH:9]=[C:8]([Cl:10])[N:7]=2)[CH2:12][CH2:13]1)=[O:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 86608290N-[1-(4-Acetyl-6-chloro-2-pyridinyl)-4-piperidinyl]-3,4-dichloro-5-methyl-1H-pyrrole-2-carboxamide

Product 1

HCID 1363325053,4-dichloro-N-[1-[6-chloro-4-[(E)-N-hydroxy-C-methylcarbonimidoyl]-2-pyridinyl]piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-[1-(4-Acetyl-6-chloropyridin-2-yl)piperidin-4-yl]-3,4-dichloro-5-methyl-1H-pyrrole-2-carboxamide (Example 115) (49 mg, 0.114 mmol) was dissolved in EtOH (2 ml). Pyridine (74 μl, 0.913 mmol) was added followed by hydroxylamine hydrochloride (63.4 mg, 0.913 mmol). The mixture was stirred at room temperature overnight. The product was purified by semi-prep reverse phase HPLC eluting with CH3CN/H2O (0.1% TFA). (28 mg).

Workup

  1. customThe product was purified by semi-prep reverse phase HPLC
  2. washeluting with CH3CN/H2O (0.1% TFA)

Sources & evidence

ORD record
ord-89c109adcfb543afa89abb601fc4d102
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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