Triethylamine → ethyl (E)-4-[2-[1-[4-[N'-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinyl]ethenyl]benzoate

HRID 354268Notes

Reaction equation

HRID 354268 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH:2]1/[CH:6]=[CH:7]/[C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=1.[CH3:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH:26][C:27](=[O:50])[NH:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][C:36](OC2C(F)=C(F)C(F)=C(F)C=2F)=[O:37])=[CH:31][CH:30]=1.CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[CH3:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH:26][C:27](=[O:50])[NH:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][C:36]([N:1]2[CH2:5][CH2:4][CH2:3][CH:2]2/[CH:6]=[CH:7]/[C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=2)=[O:37])=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 23512272pentafluorophenyl 4-[N'-(2-methylphenyl)ureido]phenylacetateHCID 86595069ethyl (E)-4-[2-(2-pyrrolidinyl)ethenyl]benzoate

Product 1

HCID 86595071ethyl (E)-4-[2-[1-[4-[N'-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinyl]ethenyl]benzoateYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl (E)-4-[2-(2-pyrrolidinyl)ethenyl]benzoate (434 mg, 1.77 mmol), pentafluorophenyl 4-[N′-(2-methylphenyl)ureido]phenylacetate (797 mg, 1.77 mmol), Et3N (0.37 mL, 2.66 mmol) in DMF (15 mL) was stirred for 15 hr. The mixture was diluted with EtOAc (300 mL). The solution was washed with brine (2×200 mL), dried over MgSO4, and evaporated off in vacuo. The residue was chromatographed on silica-gel with CHCl3-EtOAc (4:1) as eluent to give 906 mg (q.y.) ethyl (E)-4-[2-[1-[4-[N′-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinyl]ethenyl]benzoate as a brown oil. 1H-NMR (CDCl3) δ1.39 (3 H, t, J=7.3 Hz), 1.83-2.20 (4 H, series of m), 2.24 (3 H, d, J=4.9 Hz), 3.63 (4 H, m), 4.36 (2 H, q, J=7.3 Hz), 4.62 and 4.84 (total 1 H, m), 6.18-6.47 (2 H, m), 7.03-8.02 (14 H, series of m).

Workup

  1. washThe solution was washed with brine (2×200 mL)
  2. dry with materialdried over MgSO4
  3. customevaporated off in vacuo
  4. customThe residue was chromatographed on silica-gel with CHCl3-EtOAc (4:1) as eluent

Sources & evidence

ORD record
ord-7d0b6cb39bd045e9a902f87389f2b5cb
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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