Diisopropylethylamine → HCID 86711578, compound

HRID 524331Notes

Reaction equation

HRID 524331 reaction equation
[Br:1][C:2]1[C:3](=[O:15])[C:4]([C:12]([OH:14])=O)=[CH:5][N:6]([CH:9]([CH3:11])[CH3:10])[C:7]=1[CH3:8].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.[CH3:50][S:51]([C:54]1[CH:61]=[CH:60][C:57]([CH2:58][NH2:59])=[CH:56][CH:55]=1)(=[O:53])=[O:52]>CN(C=O)C.CO.C(O)(=O)C>[CH3:50][S:51]([C:54]1[CH:61]=[CH:60][C:57]([CH2:58][NH:59][C:12]([C:4]2[C:3](=[O:15])[C:2]([Br:1])=[C:7]([CH3:8])[N:6]([CH:9]([CH3:10])[CH3:11])[CH:5]=2)=[O:14])=[CH:56][CH:55]=1)(=[O:52])=[O:53]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 27292694-Methylsulfonylbenzylamine hydrochlorideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 867115775-Bromo-1-isopropyl-6-methyl-4-oxo-1,4-dihydropyridine-3-carboxylic acid

Product 1

HCID 86711578HCID 86711578, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-bromo-1-isopropyl-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (preparation 3c, 0.50 g, 1.82 mmol), HBTU (0.77 g, 2.03 mmol), DIPEA (0.76 mL, 4.47 mmol) in DMF (2 mL) is stirred for 10 min. Then, 4-methylsulfonylbenzylamine hydrochloride (0.64 g, 2.89 mmol) is added and the reaction mixture is stirred for 72 h at room temperature. The reaction mixture is diluted with methanol, acidified with acetic acid and purified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.1% TFA, 60° C.). Yield: 0.25 g (31% of theory); ESI mass spectrum: [M+H]+=441 (bromine isotope pattern); Retention time HPLC: 1.16 min (Z002_006).

Workup

  1. custompurified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.1% TFA, 60° C.)
  2. custom1.16 min (Z002_006)

Sources & evidence

ORD record
ord-9ee55156bda64e9b85d9075772213a1f
Source dataset
uspto-grants-2016_05
Patent number
US09340507B2

Reaction notes

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