Triethylamine → tert-Butyl cis(+/-)-3-chloro-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidine-1-carboxylate

HRID 1425305Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1425305
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@H:3]1[Cl:15].[Cl:16][C:17]1[N:18]=[C:19]([C:24](O)=[O:25])[NH:20][C:21]=1[CH2:22][CH3:23].O.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>>[Cl:15][C@H:3]1[C@@H:2]([NH:1][C:24]([C:19]2[NH:20][C:21]([CH2:22][CH3:23])=[C:17]([Cl:16])[N:18]=2)=[O:25])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])[CH2:4]1

Komponenten

6

Edukt 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acidHCID 86648772Tert-butyl cis(+/-)-4-amino-3-chloropiperidine-1-carboxylate

Produkt 1

HCID 86648771tert-Butyl cis(+/-)-3-chloro-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidine-1-carboxylateAusbeute 73,4 %

Versuchsvorschrift

The same operation as in Example (196b) was performed using tert-butyl cis(±)-4-amino-3-chloropiperidine-1-carboxylate obtained in Example (198a) (134 mg, 0.571 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (1d) (99.7 mg, 0.571 mmol), 1-hydroxybenzotriazole hydrate (116 mg, 0.856 mmol), WSC hydrochloride (164 mg, 0.856 mmol) and triethylamine (119 μL, 0.856 mmol), to obtain 164 mg of the title compound (73%) as a colorless solid.

Quellen und Nachweise

ORD-Eintrag
ord-cd953b57da3646a8bb7f10502058f6d4
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927588B2

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