Diisopropylethylamine → 5-Bromo-1-isopropyl-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid 4-(N-cyano-S-methylsulfonimidoyl)-benzylamide

HRID 527337Notes

Reaction equation

HRID 527337 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.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[C:47]([N:49]=[S:50]([C:53]1[CH:58]=[CH:57][C:56]([CH2:59][NH2:60])=[CH:55][CH:54]=1)([CH3:52])=[O:51])#[N:48]>CN(C=O)C>[C:47]([N:49]=[S:50]([C:53]1[CH:58]=[CH:57][C:56]([CH2:59][NH:60][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:55][CH:54]=1)([CH3:52])=[O:51])#[N:48]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 867115775-Bromo-1-isopropyl-6-methyl-4-oxo-1,4-dihydropyridine-3-carboxylic acidHCID 86711611(4-(N-cyano-S-methylsulfonimidoyl)phenyl)methanamine

Product 1

HCID 899789285-Bromo-1-isopropyl-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid 4-(N-cyano-S-methylsulfonimidoyl)-benzylamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 5-bromo-1-isopropyl-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (preparation 1c, 270 mg, 0.99 mmol), TBTU (316 mg, 0.99 mmol) and DIPEA (513 μL, 2.97 mmol) in DMF (3.00 mL) is stirred for 10 min at room temperature. Then, a solution of (4-(N-cyano-S-methylsulfonimidoyl)phenyl)methanamine (preparation 6, 247 mg, 1.18 mmol) in DMF (1.00 mL) is added and the reaction mixture is stirred for 18 h at room temperature. The reaction mixture is purified by preparative reversed phase HPLC (Sunfire, gradient of acetonitrile in water, 0.1% TFA, 60° C.). Yield: 70 mg (15% of theory); ESI mass spectrum: [M+H]+=465 (bromine isotope pattern); r.t. HPLC: 0.86 min (Z017_S04).

Workup

  1. customThe reaction mixture is purified by preparative reversed phase HPLC (Sunfire, gradient of acetonitrile in water, 0.1% TFA, 60° C.)
  2. customr.t
  3. custom0.86 min (Z017_S04)

Sources & evidence

ORD record
ord-562486d045764bdf814781ccef78e138
Source dataset
uspto-grants-2016_05
Patent number
US09346794B1

Reaction notes

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