N-methyl-2-pyrrolidone → 4'-Methyl-5-nitro-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide

HRID 340611Notes

Reaction equation

HRID 340611 reaction equation
CCN=C=NCCCN(C)C.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[C:21]([C:28]([OH:30])=O)[CH:20]=2)=[CH:15][CH:14]=1.C1C=[CH:33][C:34]2[N:39](O)N=N[C:35]=2C=1.CN1[C:46](=[O:47])CCC1>C(Cl)Cl.CN(C=O)C>[CH3:46][O:47][CH2:33][CH:34]([NH:39][C:28]([C:21]1[CH:20]=[C:19]([C:16]2[CH:15]=[CH:14][C:13]([CH3:12])=[CH:18][CH:17]=2)[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=1)=[O:30])[CH3:35]

Participants

7

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 532248984'-Methyl-5-nitro-[1,1'-biphenyl]-3-carboxylic acid

Product 1

HCID 595997024'-Methyl-5-nitro-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amideYield 83.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

EDCI (16.17 g, 84.38 mmol) was added portion wise to a stirred solution of 4′-methyl-5-nitro-biphenyl-3-carboxylic acid (15.49 g, 60.27 mmol), HOBt (11.44 g, 84.38 mmol) and 2-amino-1-methoxy-1-propane (7 ml, 66.31 mmol) in NMP (9.29 ml, 84.38 mmol), CH2Cl2 (180 ml) and DMF (20 ml) at 0° C. The mixture was allowed to warm to room temperature and was stirred at the same temperature for 14 hours. The reaction mixture was washed with 2N HCl, 2N NaOH, saturated aqueous NaHCO3, brine, dried over anhydrous Na2SO4, filtered, and concentrated under vacuum to give 4′-methyl-5-nitro-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide as a yellow oil (16.5 g, 83.5%). MS (M+H)=329.

Workup

  1. washThe reaction mixture was washed with 2N HCl, 2N NaOH, saturated aqueous NaHCO3, brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-aea7f1a66a6849fabc919c5baed147aa
Source dataset
uspto-grants-2014_11
Patent number
US08895589B2

Reaction notes

Loading…