Pentafluorophenyl 4-bromo-5-methyl-1H-pyrrole-2-carboxylate → 4-Bromo-N-{1-[6-chloro-4-(5-oxo-2,5-dihydro-1,3,4-oxadiazol-2-yl)pyridin-2-yl]piperidin-4-yl}-5-methyl-1H-pyrrole-2-carboxamide

HRID 2233953Notes

Reaction equation

HRID 2233953 reaction equation
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[C:13]([CH:15]3[O:19][C:18](=[O:20])[N:17]=[N:16]3)[CH:12]=[C:11]([Cl:21])[N:10]=2)[CH2:5][CH2:4]1.[Br:22][C:23]1[CH:24]=[C:25]([C:29](OC2C(F)=C(F)C(F)=C(F)C=2F)=[O:30])[NH:26][C:27]=1[CH3:28]>CC(N(C)C)=O>[Br:22][C:23]1[CH:24]=[C:25]([C:29]([NH:2][CH:3]2[CH2:8][CH2:7][N:6]([C:9]3[CH:14]=[C:13]([CH:15]4[N:16]=[N:17][C:18](=[O:20])[O:19]4)[CH:12]=[C:11]([Cl:21])[N:10]=3)[CH2:5][CH2:4]2)=[O:30])[NH:26][C:27]=1[CH3:28]

Participants

4

Reactant 2

HCID 86608241Pentafluorophenyl 4-bromo-5-methyl-1H-pyrrole-2-carboxylate2×HCID 866082465-[2-(4-Aminopiperidin-1-yl)-6-chloropyridin-4-yl]-1,3,4-oxadiazol-2(5H)-one hydrochloride2×

Product 1

HCID 866083074-Bromo-N-{1-[6-chloro-4-(5-oxo-2,5-dihydro-1,3,4-oxadiazol-2-yl)pyridin-2-yl]piperidin-4-yl}-5-methyl-1H-pyrrole-2-carboxamideYield 11.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

TEA (0.10 ml, 0.70 mmol) and 5-[2-(4-aminopiperidin-1-yl)-6-chloropyridin-4-yl]-1,3,4-oxadiazol-2(5H)-one hydrochloride (Intermediate 51, 0.10 g, 0.33 mmol) were added to a solution of pentafluorophenyl 4-bromo-5-methyl-1H-pyrrole-2-carboxylate (Intermediate 17) (0.12 g, 0.33 mmol) in DMA (2 ml). The mixture was stirred at room temperature overnight and was purified by semi-preparative HPLC eluting with water/acetonitrile and TFA mixtures to give the title compound (18 mg).

Workup

  1. customwas purified by semi-preparative HPLC
  2. washeluting with water/acetonitrile and TFA mixtures

Sources & evidence

ORD record
ord-99541edff3474f29a6fdde7c1963dae3
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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