Hydrochloric Acid → Ethyl 4-((2-(4-fluorophenyl)-3-(3,4,5-trimethoxyphenyl)acrylamido)methyl)benzoate

HRID 444724Notes

Reaction equation

HRID 444724 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[C:15]([OH:17])=O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH2:25]([O:27][C:28](=[O:37])[C:29]1[CH:34]=[CH:33][C:32]([CH2:35][NH2:36])=[CH:31][CH:30]=1)[CH3:26].Cl.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:14](=[CH:13][C:5]2[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:15]([NH:36][CH2:35][C:32]2[CH:31]=[CH:30][C:29]([C:28]([O:27][CH2:25][CH3:26])=[O:37])=[CH:34][CH:33]=2)=[O:17])=[CH:19][CH:20]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 436161Ethyl 4-(aminomethyl)benzoateHCID 68490939HCID 68490939, compound

Product 1

HCID 68490940Ethyl 4-((2-(4-fluorophenyl)-3-(3,4,5-trimethoxyphenyl)acrylamido)methyl)benzoateYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(3,4,5-trimethoxyphenyl)-2-(4-fluorophenyl)acrylic acid (0.6 g, 18 mmol) in DMF (5 mL) was added ethyl-4-aminomethylbenzoate.HCl (0.375 g, 21.6 mmol), EDCI (0.69 g, 36 mmol) and HOBt (0.24 g, 18 mmol). TEA (0.75 mL, 36 mmol) was added dropwise with constant stirring to the above reaction mixture and stirred overnight at room temperature. Subsequently the reaction mixture was evaporated to dryness, the residue was dissolved in ethyl acetate and washed successively with 1N HCl (3×50 mL), saturated NaHCO3 (3×50 mL) and brine solution (3×50 mL). The organic layer was dried over Na2SO4 and concentrated to give the pure compound (0.4 g, 50% yield).

Workup

  1. stirringstirred overnight at room temperature
  2. customSubsequently the reaction mixture was evaporated to dryness
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed successively with 1N HCl (3×50 mL), saturated NaHCO3 (3×50 mL) and brine solution (3×50 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9725bb1ec9354aa2b7b6eb9bd7ae40b1
Source dataset
uspto-grants-2013_07
Patent number
US08476255B2

Reaction notes

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