Diisopropylethylamine → N-(2,4-dimethoxybenzyl)-N-phenyl-4-diethylphosphoryloxy-1,2-dihydro-1-methyl-2-oxo-quinoline-3-carboxamide

HRID 1852418Notes

Reaction equation

HRID 1852418 reaction equation
[CH2:1]([P:3](Cl)([CH2:5][CH3:6])=[O:4])[CH3:2].C(N(C(C)C)C(C)C)C.[CH3:17][O:18][C:19]1[CH:47]=[C:46]([O:48][CH3:49])[CH:45]=[CH:44][C:20]=1[CH2:21][N:22]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:23]([C:25]1[C:26](=[O:37])[N:27]([CH3:36])[C:28]2[C:33]([C:34]=1[OH:35])=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:24]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:17][O:18][C:19]1[CH:47]=[C:46]([O:48][CH3:49])[CH:45]=[CH:44][C:20]=1[CH2:21][N:22]([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:23]([C:25]1[C:26](=[O:37])[N:27]([CH3:36])[C:28]2[C:33]([C:34]=1[O:35][P:3]([CH2:5][CH3:6])([CH2:1][CH3:2])=[O:4])=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:24]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 5195381Diethylphosphinoyl chlorideHCID 68186825N-(2,4-dimethoxybenzyl)-N-phenyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxamide

Product 1

HCID 86691492N-(2,4-dimethoxybenzyl)-N-phenyl-4-diethylphosphoryloxy-1,2-dihydro-1-methyl-2-oxo-quinoline-3-carboxamideYield 71.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Diethylphosphorylchloride (150 mg, 0.87 mmol) was added to a solution of EtNiPr2 (129 mg, 1.00 mmol), DMAP (10 mg, 0.08 mmol) and N-(2,4-dimethoxybenzyl)-N-phenyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxamide (222 mg, 050 mmol) in CH2Cl2 (3.0 mL). The reaction mixture was stirred for 30 min and was then concentrated at reduced pressure. The residue was purified by silica column chromatography (EtOAc) to give the title compound (196 mg, 68%).

Workup

  1. concentrationwas then concentrated at reduced pressure
  2. customThe residue was purified by silica column chromatography (EtOAc)

Sources & evidence

ORD record
ord-5646df4f509147f48fe32d46b041294a
Source dataset
uspto-grants-2015_02
Patent number
US08962598B2

Reaction notes

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