Triethylamine → ethyl 3-methoxy-4-[2-[3-methoxy-4-[N'-(2-fluorophenyl)ureido]phenylacetyl]ethylaminoethoxy]benzoate

HRID 354480Notes

Reaction equation

HRID 354480 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([OH:23])=O)[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19])=[O:11].[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:34]=[CH:35][C:36]=1[O:37][CH2:38][CH2:39][NH:40][CH2:41][CH3:42])[C:29]([O:31][CH2:32][CH3:33])=[O:30].CCN(CC)CC>>[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:34]=[CH:35][C:36]=1[O:37][CH2:38][CH2:39][NH:40][CH2:41][CH2:42][C:21](=[O:23])[CH2:20][C:5]1[CH:6]=[CH:7][C:8]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])=[O:11])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 23511825HCID 23511825, compoundHCID 23512488Ethyl 3-methoxy-4-(2-ethylaminoethoxy)benzoate

Product 1

HCID 69333489ethyl 3-methoxy-4-[2-[3-methoxy-4-[N'-(2-fluorophenyl)ureido]phenylacetyl]ethylaminoethoxy]benzoateYield 100.7%

Procedure

To a stirred solution of pentafluorophenyl ester of 3-methoxy-4-[N′-(2-fluorophenyl)ureido]phenylacetic acid (135 mg, 0.28 mmol) and ethyl 3-methoxy-4-(2-ethylaminoethoxy)benzoate (78 mg, 0.29 mmol) was added Et3N (0.1 mL, 0.72 mmol), and the resulting mixture was stirred overnight. The mixture was diluted with EtoAc, washed successively with 0.5N HCl, brine, dried over Na2SO4, and evaporated. The residue was purified by column chromatography on silica-gel with CHCl3—MeOH (50:1, v/v) as eluent to give 160 mg (q.y.) ethyl 3-methoxy-4-[2-[3-methoxy-4-[N′-(2-fluorophenyl)ureido]phenylacetyl]ethylaminoethoxy]benzoate as an oil. 1H-NMR (CDCl3) d 1.13-1.23 (m, 3 H), 1.37-1.40 (m, 3 H), 2.90-3.89 (m, 12 H), 4.09-4.28 (m, 2 H), 4.33-4.39 (m, 2 H), 6.70-8.21 (series of m, total 12 H).

Workup

  1. additionThe mixture was diluted with EtoAc
  2. washwashed successively with 0.5N HCl, brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica-gel with CHCl3—MeOH (50:1

Sources & evidence

ORD record
ord-6a2fb41633694c28b1cffb1db3e1526c
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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