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

HRID 524338Notes

Reaction equation

HRID 524338 reaction equation
BrC1C(=O)C(C(O)=O)=CN(C(C)C)C=1C.[Br:16][C:17]1[C:18](=[O:32])[C:19]([C:29]([OH:31])=O)=[CH:20][N:21]([CH:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[C:22]=1[CH3:23].Cl.CS(C1C=CC(CN)=CC=1)(=O)=O.[CH3:46][S:47]([C:50]1[CH:51]=[CH:52][C:53]([CH2:56][NH2:57])=[N:54][CH:55]=1)(=[O:49])=[O:48].BrBr>>[CH3:46][S:47]([C:50]1[CH:51]=[CH:52][C:53]([CH2:56][NH:57][C:29]([C:19]2[C:18](=[O:32])[C:17]([Br:16])=[C:22]([CH3:23])[N:21]([CH:24]([CH2:25][CH3:26])[CH2:27][CH3:28])[CH:20]=2)=[O:31])=[N:54][CH:55]=1)(=[O:49])=[O:48]

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 867115915-Bromo-1-(1-ethyl-propyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid

Product 1

HCID 867115905-Bromo-1-(1-ethyl-propyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (5-methanesulfonyl-pyridin-2-ylmethyl)-amide

Procedure

Preparation 23 is prepared following the procedure for preparation 5, substituting preparation 3c with preparation 15b and 4-methylsulfonylbenzylamine hydrochloride with C-(5-methanesulfonyl-pyridin-2-yl)-methylamine. ESI mass spectrum: [M+H]+=470 (bromine isotope pattern); Retention time HPLC: 0.91 min (Z018_S04).

Workup

  1. customPreparation 23
  2. customis prepared
  3. customfor preparation 5
  4. custom0.91 min (Z018_S04)

Sources & evidence

ORD record
ord-74ba7b1e08e24020a4f21dae5921542d
Source dataset
uspto-grants-2016_05
Patent number
US09340507B2

Reaction notes

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