1-Hydroxybenzotriazole → Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-methyl-1,3-oxazole-5-carboxylate

HRID 43621

Reaktionsgleichung

Reaktionsgleichung von HRID 43621
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]2[O:9][C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:11]([CH3:13])[N:12]=2)[CH2:4][C@H:3]1[O:19][CH3:20].[Cl:21][C:22]1[N:23]=[C:24]([C:29](O)=[O:30])[NH:25][C:26]=1[CH2:27][CH3:28].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>ClCCl.CC(N(C)C)=O>[Cl:21][C:22]1[N:23]=[C:24]([C:29]([NH:1][C@H:2]2[CH2:7][CH2:6][N:5]([C:8]3[O:9][C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:11]([CH3:13])[N:12]=3)[CH2:4][C@H:3]2[O:19][CH3:20])=[O:30])[NH:25][C:26]=1[CH2:27][CH3:28]

Komponenten

7

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acidHCID 86648585Ethyl cis(+/-)-2-(4-amino-3-methoxypiperidin-1-yl)-4-methyl-1,3-oxazole-5-carboxylate

Produkt 1

HCID 86648587Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-methyl-1,3-oxazole-5-carboxylateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

The same operation as in Example (106d) was performed using ethyl cis(±)-2-(4-amino-3-methoxypiperidin-1-yl)-4-methyl-1,3-oxazole-5-carboxylate obtained in Example (107b) (0.22 g, 0.78 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid (0.16 g, 0.92 mmol), WSC hydrochloride (0.46 g, 2.4 mmol), HOBt (0.2 g, 1.2 mmol), DMA (3 mL) and dichloromethane (3 mL). The resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/2, 1/1, 2/1, 1/0, ethyl acetate/methanol=97/3, 93/7) to obtain 0.24 g of the title compound as a light yellow solid (70%).

Aufarbeitung

  1. customThe resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/2, 1/1, 2/1, 1/0, ethyl acetate/methanol=97/3, 93/7)

Quellen und Nachweise

ORD-Eintrag
ord-d8d72ff2c2a0481cbef4bda1c5a882cc
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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