Water → HCID 66961722, compound

HRID 2247630Notes

Reaction equation

HRID 2247630 reaction equation
[H-].[Na+].CN(C=O)C.[F:8][C:9]1[CH:10]=[C:11]([C@@H:15]([NH:17][C:18](=[O:39])[C:19](=[CH:24][C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]3)=[C:27]([O:37][CH3:38])[CH:26]=2)[CH2:20][CH2:21][CH2:22]Cl)[CH3:16])[CH:12]=[CH:13][CH:14]=1.O>C(OCC)(=O)C>[F:8][C:9]1[CH:10]=[C:11]([C@H:15]([N:17]2[CH2:22][CH2:21][CH2:20]/[C:19](=[CH:24]\[C:25]3[CH:30]=[CH:29][C:28]([N:31]4[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]4)=[C:27]([O:37][CH3:38])[CH:26]=3)/[C:18]2=[O:39])[CH3:16])[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 66961663HCID 66961663, compound

Product 1

HCID 66961722HCID 66961722, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a DMF (3 mL) solution of (E)-5-chloro-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)valeric acid trifluoroacetic acid salt (100 mg) obtained according to the method described in Example 418 and (S)-1-(3-fluorophenyl)ethylamine hydrochloric acid salt (31 mg), IPEA (0.2 mL) and HOBT (36 mg) and EDC (51 mg) were added, and the reaction solution was agitated at room temperature for 3 hours. Saturated sodium bicarbonate water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. The organic layer obtained was dried over magnesium sulfate and concentrated under reduced pressure. By purifying the residue with silica gel chromatography (Carrier: Chromatorex™ NH, elution solvent: heptane:ethyl acetate 1:1->ethyl acetate), 79 mg of 5-chloro-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)valeric acid ((1S)-1-(3-fluorophenyl)ethyl)amide was obtained. Sodium hydride (40% mineral oil content, 8 mg) was added to the DMF (3 mL) solution of 5-chloro-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)valeric acid ((1S)-1-(3-fluorophenyl)ethyl)amide obtained, and the reaction solution was agitated at room temperature for 5 minutes. Water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. The organic layer obtained was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (Carrier: Chromatorex™ NH, elution solvent: heptane:ethyl acetate system 1:1->ethyl acetate) to obtain 48 mg of the racemic title compound. The physical properties of the compound are as follows.

Workup

  1. customobtained
  2. customthe organic layer was partitioned
  3. customThe organic layer obtained
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel chromatography (Carrier: Chromatorex™ NH, elution solvent: heptane:ethyl acetate system 1:1->ethyl acetate)

Sources & evidence

ORD record
ord-76badec81ea64215b66012fdb9bc89a1
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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