Triethylamine → N-(3,4-Dimethoxy-phenyl)-2-methyl-2-phenyl-N-[2-(4-trifluoromethyl-phenyl)-ethyl]-malonamic acid ethyl ester

HRID 1784148Notes

Reaction equation

HRID 1784148 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:24]([O:26][C:27](=[O:39])[C:28]([C:36](Cl)=[O:37])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH3:29])[CH3:25].C(N(CC)CC)C>>[CH2:24]([O:26][C:27](=[O:39])[C:28]([CH3:29])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:36]([N:11]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:22])([F:21])[F:23])=[CH:16][CH:15]=1)=[O:37])[CH3:25]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 57591499HCID 57591499, compound2×HCID 866236412-Chlorocarbonyl-2-phenyl-propionic acid ethyl ester

Product 1

HCID 67084343N-(3,4-Dimethoxy-phenyl)-2-methyl-2-phenyl-N-[2-(4-trifluoromethyl-phenyl)-ethyl]-malonamic acid ethyl esterYield 45%

Procedure

A mixture of 97.5 mg (0.3 mmol) (3,4-dimethoxy-phenyl)-[2-(4-trifluoromethyl-phenyl)-ethyl]-amine (intermediate 1), 101 mg (0.45 mmol) 2-chlorocarbonyl-2-phenyl-propionic acid ethyl ester (Journal of Organic Chemistry (1959), 24 109-10) and 121 mg (1.2 mmol) triethylamine 15 mL DCM was stirred for 16 h at room temperature. The mixture was evaporated and purified by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and formic acid, the product containing fractions were evaporated to yield 71.5 mg (45%) of the title compound. MS(m/e): 530.2 (MH+).

Workup

  1. customThe mixture was evaporated
  2. custompurified by preparative HPLC on reversed phase
  3. washeluting with a gradient
  4. customformed from acetonitrile, water and formic acid
  5. additionthe product containing fractions
  6. customwere evaporated

Sources & evidence

ORD record
ord-a175a90011cb4823bf69fdab4ee0fdf5
Source dataset
uspto-grants-2009_03
Patent number
US07501541B2

Reaction notes

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