Triethylamine → methyl 3-(E)(4-(3-(cyclopropylamino)-2-(4-fluorophenyl)-3-oxoprop-1-en-1-yl)phenyl)acrylate

HRID 2098565Notes

Reaction equation

HRID 2098565 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH:12][C:13]2[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])=[CH:15][CH:14]=2)[C:9](O)=[O:10])=[CH:4][CH:3]=1.[CH:25]1([NH2:28])[CH2:27][CH2:26]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[CH:25]1([NH:28][C:9](=[O:10])[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:12][C:13]2[CH:14]=[CH:15][C:16](/[CH:19]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])=[CH:17][CH:18]=2)[CH2:27][CH2:26]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 68771470HCID 68771470, compound

Product 1

HCID 68766754methyl 3-(E)(4-(3-(cyclopropylamino)-2-(4-fluorophenyl)-3-oxoprop-1-en-1-yl)phenyl)acrylateYield 114%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(4-fluorophenyl)-3-(4-((E)-3-methoxy-3-oxoprop-1-en-1-yl)phenyl)acrylic acid (0.23 g, 0.71 mmol) and cyclopropylamine (0.03 g, 0.60 mmol), EDCI (0.27 g, 1.4 mmol), HOBt (0.10 g, 0.71 mmol) was dissolved in N,N-dimethylformamide (DMF) (6 mL) under stirring. Triethylamine (TEA) (0.75 mL, 36 mmol) was added dropwise with constant stirring to the above reaction mixture and it was stirred at 30° C. for 2 hours. Subsequently the reaction mixture was diluted with ethyl acetate and washed successively with water (3×50 mL) and brine (3×50 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to afford the pure compound (0.25 g, 96% yield).

Workup

  1. stirringwith constant stirring to the above reaction mixture and it
  2. stirringwas stirred at 30° C. for 2 hours
  3. washwashed successively with water (3×50 mL) and brine (3×50 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bf25f2921b6b4e0486b902bd90bb160e
Source dataset
uspto-grants-2013_05
Patent number
US08450525B2

Reaction notes

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