Pyridine → N-(3,4-Dimethoxy-phenyl)-N'-methyl-2-phenyl-N-[2-(4-trifluoromethyl-phenyl)-ethyl]-malonamide

HRID 1784146Notes

Reaction equation

HRID 1784146 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:11]([CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)[C:12](=[O:23])[CH:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14](O)=[O:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CN.[CH3:38][N:39](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.N1C=CC=CC=1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:11]([CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)[C:12](=[O:23])[CH:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]([NH:39][CH3:38])=[O:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6329MethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 57591457N-(3,4-Dimethoxy-phenyl)-2-phenyl-N-[2-(4-trifluoromethyl-phenyl)-ethyl]-malonamic acid

Product 1

HCID 25014479N-(3,4-Dimethoxy-phenyl)-N'-methyl-2-phenyl-N-[2-(4-trifluoromethyl-phenyl)-ethyl]-malonamideYield 16.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 16.2 mg (0.033 mmol) N-(3,4-Dimethoxy-phenyl)-2-phenyl-N-[2-(4-trifluoromethyl-phenyl)-ethyl]-malonamic acid, 15.5 mg (0.049 mmol) methylamine (commercially available), 13.8 mg (0.043 mmol) TBTU and 7.8 mg (0.09 mmol) pyridine in 2 mL DMF was shaken for 4 h at room temperature. The mixture was evaporated to dryness, taken up in methanol, formic acid and subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and acetic acid. The combined product fractions were evaporated to dryness to yield 2.7 mg (16%) of the title compound. MS(m/e): 501.3 (MH+), MH+ found: 501.3.

Workup

  1. customThe mixture was evaporated to dryness
  2. customformic acid and subjected to purification by preparative HPLC on reversed phase
  3. washeluting with a gradient
  4. customformed from acetonitrile, water and acetic acid
  5. customThe combined product fractions were evaporated to dryness

Sources & evidence

ORD record
ord-4b9d3f93ebc54ec0bf7376c8f134501f
Source dataset
uspto-grants-2009_03
Patent number
US07501541B2

Reaction notes

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