2,4-Difluorophenyl isocyanate → 3-(4-{2-[3-(2,4-difluorophenyl)-1-heptylureido]ethoxy}phenyl)-2-ethoxypropionic Acid Ethyl Ester

HRID 1744459Notes

Reaction equation

HRID 1744459 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH:5]([O:24][CH2:25][CH3:26])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:9][CH:8]=1)[CH3:2].[F:28][C:29]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=1[N:36]=[C:37]=[O:38]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:27])[CH:5]([O:24][CH2:25][CH3:26])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][N:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:37]([NH:36][C:30]2[CH:31]=[CH:32][C:33]([F:35])=[CH:34][C:29]=2[F:28])=[O:38])=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 5932582,4-Difluorophenyl isocyanateHCID 696257582-Ethoxy-3-[4-(2-heptylaminoethoxy)phenyl]propionic acid ethyl ester

Product 1

HCID 102395753-(4-{2-[3-(2,4-difluorophenyl)-1-heptylureido]ethoxy}phenyl)-2-ethoxypropionic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the compound obtained in Step e (30.9 mg) in methylene chloride (2 ml) was added with 2,4-difluorophenyl isocyanate (14 μl, Aldrich) and stirred for 16 hours. The reaction mixture was concentrated, and the resulting residue was applied on a silica gel column and eluted with hexane/ethyl acetate (4:1) to obtain the title compound (41.6 mg).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washeluted with hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-eee8f27af11749609f8fd66faf36f312
Source dataset
uspto-grants-2006_03
Patent number
US07015345B2

Reaction notes

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