1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-4-[3-(4-hydroxy-piperidin-1-yl)-3-oxo-propyl]-[1,4]diazepan-5-one

HRID 2095531Notes

Reaction equation

HRID 2095531 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])[N:16]([CH2:21][CH2:22][C:23]([OH:25])=O)[CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[OH:26][CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.CCN=C=NCCCN(C)C>ClCCl>[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])[N:16]([CH2:21][CH2:22][C:23]([N:30]3[CH2:31][CH2:32][CH:27]([OH:26])[CH2:28][CH2:29]3)=[O:25])[CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 79341Piperidin-4-olHCID 670745383-{4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-propionic acid2×

Product 1

HCID 582321611-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-4-[3-(4-hydroxy-piperidin-1-yl)-3-oxo-propyl]-[1,4]diazepan-5-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.100 g (0.26 mmol) of 3-{4-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-propionic acid (intermediate 5) and 0.032 g (0.31 mmol) of 4-hydroxypiperidine in 5 ml of dichloromethane was treated at 0° C. with 0.060 g (0.31 mmol) of EDCI. The cooling bath was allowed to come to RT and after 4 h the reaction was extracted with aqueous 10% KHSO4/EtOAc (3×). The organic phases were washed with aqueous saturated NaHCO3, 10% NaCl and dried over Na2SO4 to yield after evaporation of the solvent 0.108 g (89%) of the titled compound as white solid. MS: 468.3 (MH+, 1Cl).

Workup

  1. extractionthe reaction was extracted with aqueous 10% KHSO4/EtOAc (3×)
  2. washThe organic phases were washed with aqueous saturated NaHCO3, 10% NaCl
  3. dry with materialdried over Na2SO4
  4. customto yield
  5. customafter evaporation of the solvent 0.108 g (89%) of the titled compound as white solid

Sources & evidence

ORD record
ord-100e0de244f74199abfc04d3669b7370
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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