Diisopropylethylamine → N-(2-chlorobenzyl)-3-(3-(4-ethylphenyl)ureido)-2,2-dimethylpropanamide

HRID 655960

Reaktionsgleichung

Reaktionsgleichung von HRID 655960
[NH2:1][CH2:2][C:3]([CH3:16])([CH3:15])[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14])=[O:5].CCN(C(C)C)C(C)C.[CH2:26]([C:28]1[CH:33]=[CH:32][C:31]([N:34]=[C:35]=[O:36])=[CH:30][CH:29]=1)[CH3:27]>C(Cl)Cl>[Cl:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH2:7][NH:6][C:4](=[O:5])[C:3]([CH3:16])([CH3:15])[CH2:2][NH:1][C:35]([NH:34][C:31]1[CH:32]=[CH:33][C:28]([CH2:26][CH3:27])=[CH:29][CH:30]=1)=[O:36]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 900074-Ethylphenyl isocyanateHCID 597784043-amino-N-(2-chlorobenzyl)-2,2-dimethylpropanamide

Produkt 1

HCID 59778437N-(2-chlorobenzyl)-3-(3-(4-ethylphenyl)ureido)-2,2-dimethylpropanamideAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-amino-N-(2-chlorobenzyl)-2,2-dimethylpropanamide (0.45 mmol) in DCM (5 mL) was added DIEA (157 μL, 0.90 mmol, 2 equiv.) and 4-ethylphenyl isocyanate (97.0 μL, 0.675 mmol, 1.5 equiv.). The reaction mixture was stirred for 30 min. The mixture was concentrated and purified on RP-HPLC using a mixture of acetonitrile and H2O to give N-(2-chlorobenzyl)-3-(3-(4-ethylphenyl)ureido)-2,2-dimethylpropanamide (29.6 mg, 17% for two steps). LRMS (M+H+) m/z 388.1.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. custompurified on RP-HPLC
  3. additiona mixture of acetonitrile and H2O

Quellen und Nachweise

ORD-Eintrag
ord-fbf95c09ddeb414896cdac53853c60c1
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071625B2

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