1-(3-Nitropyridin-2-yl)piperidin-4-amine hydrochloride → 4-Bromo-5-Methyl-N-[1-(3-Nitropyridin-2-Yl)piperidin-4-Yl]-1h-Pyrrole-2-Carboxamide

HRID 2233947Notes

Reaction equation

HRID 2233947 reaction equation
Cl.[N+:2]([C:5]1[C:6]([N:11]2[CH2:16][CH2:15][CH:14]([NH2:17])[CH2:13][CH2:12]2)=[N:7][CH:8]=[CH:9][CH:10]=1)([O-:4])=[O:3].[Br:18][C:19]1[CH:20]=[C:21]([C:25](OC2C(F)=C(F)C(F)=C(F)C=2F)=[O:26])[NH:22][C:23]=1[CH3:24]>CC(N(C)C)=O>[Br:18][C:19]1[CH:20]=[C:21]([C:25]([NH:17][CH:14]2[CH2:15][CH2:16][N:11]([C:6]3[C:5]([N+:2]([O-:4])=[O:3])=[CH:10][CH:9]=[CH:8][N:7]=3)[CH2:12][CH2:13]2)=[O:26])[NH:22][C:23]=1[CH3:24]

Participants

4

Reactant 2

HCID 457890031-(3-Nitropyridin-2-yl)piperidin-4-amine hydrochloride2×HCID 86608241Pentafluorophenyl 4-bromo-5-methyl-1H-pyrrole-2-carboxylate2×

Product 1

HCID 547591604-Bromo-5-Methyl-N-[1-(3-Nitropyridin-2-Yl)piperidin-4-Yl]-1h-Pyrrole-2-Carboxamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

1-(3-Nitropyridin-2-yl)piperidin-4-amine hydrochloride salt (Intermediate 39) (41 mg, 1.35 mmol) and TEA (37 μl, 1.35 mmol) were added to pentafluorophenyl 4-bromo-5-methyl-1H-pyrrole-2-carboxylate (Intermediate 17): (50 mg, 1.35 mmol) in anhydrous DMA (1 ml). The mixture was stirred at room temperature overnight. The crude mixture was filtered and purified by semi-preparative HPLC using CH3CN/H2O (0.1% TFA) to yield the title compound as a yellow solid (26 mg).

Workup

  1. filtrationThe crude mixture was filtered
  2. custompurified by semi-preparative HPLC

Sources & evidence

ORD record
ord-d356dc843460494e91e6541221928ed9
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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