Diisopropylethylamine → HCID 68869926, compound

HRID 2112065Notes

Reaction equation

HRID 2112065 reaction equation
[CH2:1]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)[CH:2]([CH3:4])[CH3:3].C(N(C(C)C)C(C)C)C.Cl[C:27](=[O:49])[CH2:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][O:38][C:39]2[CH:48]=[CH:47][CH:46]=[CH:45][C:40]=2[C:41]([O:43][CH3:44])=[O:42])=[CH:32][CH:31]=1>C(#N)C>[CH2:1]([N:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]([F:14])([F:15])[F:16])=[CH:11][CH:12]=1)[C:27](=[O:49])[CH2:28][O:29][C:30]1[CH:31]=[CH:32][C:33]([CH2:36][CH2:37][O:38][C:39]2[CH:48]=[CH:47][CH:46]=[CH:45][C:40]=2[C:41]([O:43][CH3:44])=[O:42])=[CH:34][CH:35]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 28428127HCID 28428127, compoundHCID 86600967Benzoic acid, 2-[2-[4-(2-chloro-2-oxoethoxy)phenyl]ethoxy]-, methyl ester

Product 1

HCID 68869926HCID 68869926, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Isobutyl-N-[4-(trifluoromethyl)benzyl]amine (0.172 g, 0.746 mol) was dissolved in dry acetonitrile under N2 and N-ethyl-N,N-diisopropylamine (0.371 g, 2.867 mmol) was added. The mixture was stirred for 30 min and methyl 2-{2-[4-(2-chloro-2-oxoethoxy)phenyl]ethoxy}benzoate (0.200 g, 0.573 mmol) was added. The solution was stirred over night at room temperature. The crude was purified by flash chromatography (started with isocratic heptane/EtOAc 50/50 and then the EtOAc concentration was increased to 100%, (silica gel 60 0.004-0.063 mm). The product containing fractions were pooled and the EtOAc was removed by evaporation to give 0.242 g of methyl 2-{2-[4-(2-{isobutyl[4-(trifluoromethyl)benzyl]amino}-2-oxoethoxy)phenyl]ethoxy}benzoate (yield 77.6%).

Workup

  1. stirringThe solution was stirred over night at room temperature
  2. customThe crude was purified by flash chromatography (
  3. concentrationthe EtOAc concentration
  4. temperaturewas increased to 100%, (silica gel 60 0.004-0.063 mm)
  5. additionThe product containing fractions
  6. customthe EtOAc was removed by evaporation

Sources & evidence

ORD record
ord-0cbd0788f56842a39e80cb5e1f9547d9
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

Loading…