Triethylamine → HCID 69333036, compound

HRID 354472Notes

Reaction equation

HRID 354472 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][NH:17][CH3:18])[C:6]([O:8][CH2:9][CH3:10])=[O:7].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH2:38][C:39](O)=[O:40])[CH:24]=[CH:25][C:26]=1[NH:27][C:28]([NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH3:37])=[O:29].CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH:16]([NH:17][CH3:18])[C:39](=[O:40])[CH2:38][C:23]1[CH:24]=[CH:25][C:26]([NH:27][C:28]([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[CH3:37])=[O:29])=[C:21]([O:20][CH3:19])[CH:22]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 114498403-Methoxy-4-o-tolylureidophenylacetic acidHCID 23511768HCID 23511768, compound

Product 1

HCID 69333036HCID 69333036, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of ethyl 3-methoxy-4-(2-methylaminoethoxy)benzoate (510 mg, 2.01 mmol) in DMF (13 mL) was added pentafluorophenyl ester of 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetic acid (900 mg, 1.87 mmol) and Et3N (0.420 mL, 3.01 mmol), and the resulting mixture was stirred for 2 days. The mixture was diluted with EtOAc, washed with 1 N HCl, sat. NaHCO3, brine, and dried over Na2SO4. After being evaporated, the residue was purified by column chromatography on silica-gel with CHCl3:MeOH (50:1, v/v) to give 880 mg (85%) ethyl 3-methoxy-4-[2-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]-N-methylaminoethoxy]benzoate as a colorless amorphous solid. 1H-NMR (CDCl3) d 1.37-1.41 (m, 3 H), 2.28 (s, 3 H), 3.03 and 3.18 (s, 3 H), 3.56 (s, 2 H), 3.65 (s, 2 H), 3.75-3.87 (m, 6 H), 4.06-4.24 (2 H, m), 4.33-4.39 (m, 2 H), 6.68-8.08 (series of m, 12 H).

Workup

  1. washwashed with 1 N HCl, sat. NaHCO3, brine
  2. dry with materialdried over Na2SO4
  3. customAfter being evaporated
  4. customthe residue was purified by column chromatography on silica-gel with CHCl3:MeOH (50:1

Sources & evidence

ORD record
ord-ba18560d2b064c03b69fac369a0e1379
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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