3-Fluorobenzylamine → (E)-5-(3-fluorobenzylamino)-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)valeric acid ethyl ester

HRID 1446497Notes

Reaction equation

HRID 1446497 reaction equation
[CH2:1]([O:3][C:4](=[O:25])/[C:5](=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]2)=[C:13]([O:23][CH3:24])[CH:12]=1)/[CH2:6][CH2:7][CH:8]=O)[CH3:2].[F:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30][NH2:31].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.C(O)(=O)C.C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:25])/[C:5](=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]2)=[C:13]([O:23][CH3:24])[CH:12]=1)/[CH2:6][CH2:7][CH2:8][NH:31][CH2:30][C:29]1[CH:32]=[CH:33][CH:34]=[C:27]([F:26])[CH:28]=1)[CH3:2]

Participants

8

Reactant 4

HCID 668533-FluorobenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86585896Sodium bicarbonate waterHCID 86602475(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]-5-oxovaleric acid ethyl ester

Product 1

HCID 66960249(E)-5-(3-fluorobenzylamino)-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)valeric acid ethyl ester

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a methylene chloride (2.0 mL) solution of (E)-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)-5-oxo-valeric acid ethyl ester (142 mg), 3-fluorobenzylamine (141 μL), acetic acid (1.0 mL) and sodium triacetoxy borohydride (105 mg) were added one by one. After agitating reaction solution at room temperature overnight, a saturated sodium bicarbonate water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (Carrier: Chromatorex™ NH, an elution solvent:ethyl acetate→ethyl acetate:ethanol=10:1), and 81 mg of the title compound was obtained. The physical properties of the compound are as follows.

Workup

  1. customreaction solution at room temperature overnight
  2. customthe organic layer was partitioned
  3. washAfter the obtained organic layer was washed with a saturated saline solution, it
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (Carrier

Sources & evidence

ORD record
ord-0dd8d6ab958d41a3b4b9cdc23426c162
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

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