6-Chloro-N-hydroxy-nicotinamidine → 2-Chloro-5-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}pyridine

HRID 1631024Notes

Reaction equation

HRID 1631024 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=O)=[CH:4][C:3]=1[CH2:12][O:13]C.[Cl:15][C:16]1[N:21]=[CH:20][C:19]([C:22](=[N:24]O)[NH2:23])=[CH:18][CH:17]=1>>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[N:24]=[C:12]([C:3]3[CH:2]=[CH:11][C:10]([C:2]4[CH:11]=[CH:10][CH:5]=[CH:4][C:3]=4[CH3:12])=[C:5]([CH2:6][O:8][CH3:9])[CH:4]=3)[O:13][N:23]=2)=[CH:20][N:21]=1

Participants

3

Reactant 2

HCID 336784996-Chloro-N-hydroxy-nicotinamidineHCID 58554220Methyl 4-bromo-3-(methoxymethyl)benzoate

Product 1

HCID 469093022-Chloro-5-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}pyridine

Procedure

The title compound was prepared following procedure described in Method B starting from Intermediate A1 and 6-chloro-N′-hydroxypyridine-3-carboximidamide (J. Med. Chem., 2005, 5215-5223). After purification by flash chromatography (silica, EtOAc/cHex), the title compound was obtained as a colorless oil (661 mg, 70%). HPLC (Method A), Rt: 5.8 min (purity: 99%). UPLC/MS, M+(ESI): 392.2.

Workup

  1. customThe title compound was prepared following procedure
  2. customAfter purification by flash chromatography (silica, EtOAc/cHex)

Sources & evidence

ORD record
ord-c1e2a3077e4d4a208d037e8d5a039b4b
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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