Diisopropylethylamine → HCID 67067420, compound

HRID 2235691Notes

Reaction equation

HRID 2235691 reaction equation
C(N(C(C)C)CC)(C)C.FC(F)(F)C(O)=O.[Cl:17][CH2:18][CH2:19][CH2:20]/[C:21](=[CH:25]\[C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH:36]=[C:35]([CH3:37])[N:34]=[CH:33]2)=[C:28]([O:38][CH3:39])[CH:27]=1)/[C:22]([OH:24])=[O:23].Cl[CH:41]([C:46]([C:48]1[CH:53]=[CH:52][C:51]([F:54])=[CH:50][CH:49]=1)=[O:47])[C:42]([O:44][CH3:45])=[O:43].O.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[Cl:17][CH2:18][CH2:19][CH2:20]/[C:21](=[CH:25]\[C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH:36]=[C:35]([CH3:37])[N:34]=[CH:33]2)=[C:28]([O:38][CH3:39])[CH:27]=1)/[C:22]([O:24][CH:41]([C:42]([O:44][CH3:45])=[O:43])[C:46]([C:48]1[CH:49]=[CH:50][C:51]([F:54])=[CH:52][CH:53]=1)=[O:47])=[O:23]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 58752226Methyl 2-chloro-3-(4-fluorophenyl)-3-oxopropionateHCID 66960186(E)-5-chloro-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)valeric acid trifluoroacetateHCID 86585896Sodium bicarbonate water

Product 1

HCID 67067420HCID 67067420, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

IPEA (1.9 mL) was added to a solution of 5-chloro-2-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}valeric acid trifluoroacetic acid salt (1.53 g) and methyl 2-chloro-3-(4-fluorophenyl)-3-oxopropionate (CAS #160727-96-8, 624 mg) in DMF (5 mL), and the reaction solution was stirred at room temperature for four hours. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane:ethyl acetate=1:1->ethyl acetate) to obtain 817 mg of the title compound. The property values of the compound are as follows.

Workup

  1. customthe organic layer was separated
  2. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (elution solvent: heptane:ethyl acetate=1:1->ethyl acetate)

Sources & evidence

ORD record
ord-413c746a1d734d1e8d0f45a6bd544949
Source dataset
uspto-grants-2010_05
Patent number
US07713993B2

Reaction notes

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