N-(2-aminoethyl)acetamide → Ethyl cis(+/-)-4-[(2-acetamidoethyl)carbamoyl]-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-1,3-thiazole-5-carboxylate

HRID 43959

Reaktionsgleichung

Reaktionsgleichung von HRID 43959
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][N:15]([C:18]3[S:19][C:20]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:21]([C:23]([OH:25])=O)[N:22]=3)[CH2:14][C@H:13]2[O:31][CH2:32][CH3:33])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].[C:34]([NH:37][CH2:38][CH2:39][NH2:40])(=[O:36])[CH3:35].CCN=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1>>[C:34]([NH:37][CH2:38][CH2:39][NH:40][C:23]([C:21]1[N:22]=[C:18]([N:15]2[CH2:16][CH2:17][C@H:12]([NH:11][C:9]([C:4]3[NH:5][C:6]([CH2:7][CH3:8])=[C:2]([Cl:1])[N:3]=3)=[O:10])[C@H:13]([O:31][CH2:32][CH3:33])[CH2:14]2)[S:19][C:20]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:25])(=[O:36])[CH3:35]

Komponenten

5

Edukt 4

HCID 66082N-(2-aminoethyl)acetamideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86648529cis(+/-)-2-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-5-(ethoxycarbonyl)-1,3-thiazole-4-carboxylic acid

Produkt 1

HCID 86648841Ethyl cis(+/-)-4-[(2-acetamidoethyl)carbamoyl]-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-1,3-thiazole-5-carboxylateAusbeute 57,4 %

Versuchsvorschrift

The same operation as in Example (247a) was performed using cis(±)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-5-(ethoxycarbonyl)-1,3-thiazole-4-carboxylic acid obtained in Example (50a) (200 mg, 0.40 mmol), N-acetylethylenediamine (0.08 mL, 0.80 mmol), WSC hydrochloride (230 mg, 1.20 mmol) and 1-hydroxybenzotriazole (54 mg, 0.40 mmol), to obtain 134 mg of the title compound as a white solid (57%).

Quellen und Nachweise

ORD-Eintrag
ord-594df789ab634739b937d425f5b532f5
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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