Ethyl bromoacetate → {4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-acetic acid ethyl ester

HRID 2095508Notes

Reaction equation

HRID 2095508 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([N:13]2[CH2:19][CH2:18][C:17](=[O:20])[NH:16][CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][N:16]1[C:17](=[O:20])[CH2:18][CH2:19][N:13]([C:11](=[O:12])/[CH:10]=[CH:9]/[C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:14][CH2:15]1)[CH3:27]

Participants

3

Reactant 2

HCID 7748Ethyl bromoacetateHCID 620449211-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-[1,4]diazepan-5-one2×

Product 1

HCID 67074624{4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-acetic acid ethyl esterYield 51%

Procedure

In analogy to the procedure described in intermediate 5B, 1-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-[1,4]diazepan-5-one (intermediate 5A) and ethyl bromoacetate gave, after purification on a SiO2-column (n-heptane/EtOAc 1:2 to 100% EtOAc), the titled compound in 51% yield as white foam. MS: 399.1 (MH+, 2Cl).

Workup

  1. customgave
  2. customafter purification on a SiO2-column (n-heptane/EtOAc 1:2 to 100% EtOAc)

Sources & evidence

ORD record
ord-68ed1951c118449d8ba516d8ba838332
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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