Bromine → 5-Bromo-1-cyclobutyl-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (5-methyl-[1,3,4]oxadiazol-2-ylmethyl)-amide

HRID 524339Notes

Reaction equation

HRID 524339 reaction equation
BrC1C(=O)C(C(O)=O)=CN(C(C)C)C=1C.[Br:16][C:17]1[C:18](=[O:31])[C:19]([C:28]([OH:30])=O)=[CH:20][N:21]([CH:24]2[CH2:27][CH2:26][CH2:25]2)[C:22]=1[CH3:23].Cl.CS(C1C=CC(CN)=CC=1)(=O)=O.[CH3:45][C:46]1[O:50][C:49]([CH2:51][NH2:52])=[N:48][N:47]=1.BrBr>>[CH3:45][C:46]1[O:50][C:49]([CH2:51][NH:52][C:28]([C:19]2[C:18](=[O:31])[C:17]([Br:16])=[C:22]([CH3:23])[N:21]([CH:24]3[CH2:25][CH2:26][CH2:27]3)[CH:20]=2)=[O:30])=[N:48][N:47]=1

Participants

6

Reactant 5

HCID 24408BromineHCID 27292694-Methylsulfonylbenzylamine hydrochlorideHCID 14442192[(5-Methyl-1,3,4-oxadiazol-2-yl)methyl]amineHCID 867115775-Bromo-1-isopropyl-6-methyl-4-oxo-1,4-dihydropyridine-3-carboxylic acidHCID 867115825-Bromo-1-cyclobutyl-6-methyl-4-oxo-1,4-dihydropyridine-3-carboxylic acid

Product 1

HCID 867115925-Bromo-1-cyclobutyl-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (5-methyl-[1,3,4]oxadiazol-2-ylmethyl)-amide

Procedure

Preparation 24 is prepared following the procedure for preparation 5, substituting preparation 3c with preparation 7b and 4-methylsulfonylbenzylamine hydrochloride with C-(5-methyl-[1,3,4]oxadiazol-2-yl)-methylamine. ESI mass spectrum: [M+H]+=381 (bromine isotope pattern); Retention time HPLC: 0.69 min (Z003_001).

Workup

  1. customPreparation 24
  2. customis prepared
  3. customfor preparation 5
  4. custom0.69 min (Z003_001)

Sources & evidence

ORD record
ord-55207b24ccc541a68fd7f3707b06984b
Source dataset
uspto-grants-2016_05
Patent number
US09340507B2

Reaction notes

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