Cyclopentanecarbonyl chloride → [5-(Benzyl-cyclopentanecarbonyl-amino)-2-propyl-benzoimidazol-1-yl]-acetic acid tert-butyl ester

HRID 15584

Reaktionsgleichung

Reaktionsgleichung von HRID 15584
[CH:1]1([C:6](Cl)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]([O:13][C:14](=[O:36])[CH2:15][N:16]1[C:20]2[CH:21]=[CH:22][C:23]([NH:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:24][C:19]=2[N:18]=[C:17]1[CH2:33][CH2:34][CH3:35])([CH3:12])([CH3:11])[CH3:10].CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl.Cl>[C:9]([O:13][C:14](=[O:36])[CH2:15][N:16]1[C:20]2[CH:21]=[CH:22][C:23]([N:25]([CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:7])=[CH:24][C:19]=2[N:18]=[C:17]1[CH2:33][CH2:34][CH3:35])([CH3:12])([CH3:11])[CH3:10]

Komponenten

7

Edukt 3

HCID 78284Cyclopentanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 67200053(5-Benzylamino-2-propyl-benzoimidazol-1-yl)-acetic acid tert-butyl ester

Produkt 1

HCID 67200357[5-(Benzyl-cyclopentanecarbonyl-amino)-2-propyl-benzoimidazol-1-yl]-acetic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Cyclopentanecarbonyl chloride (43 μL, 0.36 mmol) was added to a solution of (5-benzylamino-2-propyl-benzoimidazol-1-yl)-acetic acid tert-butyl ester (45 mg, 0.12 mmol), DIEA (41 μL, 0.24 mmol) and DMAP (15 mg, 0.12 mmol) in CH2Cl2 (1 mL), and stirred overnight at room temperature. The reaction solution was diluted with aqueous HCl (1.0 M) and filtered through an Extrelut column. The Extrelut column was washed with CH2Cl2, and the filtrate was concentrated to afford the subtitle compound that was used without further purification. MS calculated for C29H37N3O3+H: 476, observed: 476.

Aufarbeitung

  1. filtrationfiltered through an Extrelut column
  2. washThe Extrelut column was washed with CH2Cl2
  3. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-d8e75d7e77ea44ca9dac7480559a22da
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732618B2

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