Bromine → (S)-5-Bromo-1-sec-butyl-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (5-methanesulfonyl-pyridin-2-ylmethyl)-amide

HRID 524335Notes

Reaction equation

HRID 524335 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]([C@H:24]([CH2:26][CH3:27])[CH3:25])[C:22]=1[CH3:23].Cl.CS(C1C=CC(CN)=CC=1)(=O)=O.[CH3:45][S:46]([C:49]1[CH:50]=[CH:51][C:52]([CH2:55][NH2:56])=[N:53][CH:54]=1)(=[O:48])=[O:47].BrBr>>[CH3:45][S:46]([C:49]1[CH:50]=[CH:51][C:52]([CH2:55][NH:56][C:28]([C:19]2[C:18](=[O:31])[C:17]([Br:16])=[C:22]([CH3:23])[N:21]([C@H:24]([CH2:26][CH3:27])[CH3:25])[CH:20]=2)=[O:30])=[N:53][CH:54]=1)(=[O:48])=[O:47]

Participants

6

Reactant 5

HCID 24408BromineHCID 27292694-Methylsulfonylbenzylamine hydrochlorideHCID 57354332(5-(Methylsulfonyl)pyridin-2-yl)methanamineHCID 867115775-Bromo-1-isopropyl-6-methyl-4-oxo-1,4-dihydropyridine-3-carboxylic acidHCID 86711586HCID 86711586, compound

Product 1

HCID 86711585(S)-5-Bromo-1-sec-butyl-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (5-methanesulfonyl-pyridin-2-ylmethyl)-amide

Procedure

Preparation 20 is prepared following the procedure for preparation 5, substituting preparation 3c with preparation 12b and 4-methylsulfonylbenzylamine hydrochloride with C-(5-methanesulfonyl-pyridin-2-yl)-methylamine. ESI mass spectrum: [M+H]+=456 (bromine isotope pattern); Retention time HPLC: 0.87 min (Z018_S04).

Workup

  1. customPreparation 20
  2. customis prepared
  3. customfor preparation 5
  4. custom0.87 min (Z018_S04)

Sources & evidence

ORD record
ord-e29899bc0b0a4cabb94a3ac740daba2d
Source dataset
uspto-grants-2016_05
Patent number
US09340507B2

Reaction notes

Loading…