p-Toluidine → HCID 57812316, compound

HRID 912055Notes

Reaction equation

HRID 912055 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[F:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([OH:38])=O)[C:31]2=[O:39])=[CH:26][CH:25]=1.[NH2:40][C:41]1[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=1.C(N(CC)CC)C>CN(C=O)C>[C:44]1([CH3:47])[CH:45]=[CH:46][C:41]([NH:40][C:36]([C:32]2[C:31](=[O:39])[N:30]([C:27]3[CH:26]=[CH:25][C:24]([F:23])=[CH:29][CH:28]=3)[CH:35]=[CH:34][CH:33]=2)=[O:38])=[CH:42][CH:43]=1

Participants

6

Reactant 4

HCID 7813p-ToluidineHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 210815271-(4-Fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Product 1

HCID 57812316HCID 57812316, compoundYield 273.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

TBTU (276 mg, 0.851 mmol) was added to the mixture of 1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (147 mg, 0.567 mmol), p-toluidine (73.7 mg, 0.681 mmol), and triethylamine (120 μl, 0.851 mmol) in DMF (3 ml) at rt. The combined mixture was stirred at rt for 16 h. After that time, the solvent was removed to give a black solid (500 mg). It was purified by chromatography on silica gel (15 g) eluting with 40% (100 ml), 50% (100 ml), 60% (100 ml) and 70% (100 ml) EtOAc/hexane to give the title compound as a light-brown solid. 1H NMR (400 MHz, CDCl3): δ=2.31 (s, 3H), 6.58 (dd, J=6.8 & 7.2 Hz, 1H), 7.13 (d, J=8.4 Hz, 2H), 7.23-7.29 (m, 2H), 7.38-7.42 (m, 2H), 7.56-7.63 (m, 3H), 8.74 (dd, J=2.0 & 6.8 Hz, 1H), 11.69 (brs, 1H). MS (ES+): m/z 323.09 [MH+]. HPLC: tR=3.69 min (polar—5 min, ZQ3).

Workup

  1. customAfter that time, the solvent was removed

Sources & evidence

ORD record
ord-bbf6afec369948dd84012c0c00ed9f45
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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