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

HRID 1425310Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1425310
[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[N:15]([CH3:17])[CH3:16].[Cl:18][C:19]1[N:20]=[C:21]([C:26](O)=[O:27])[NH:22][C:23]=1[CH2:24][CH3:25].O.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>>[Cl:18][C:19]1[N:20]=[C:21]([C:26]([NH:1][C@H:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4][C@H:3]2[N:15]([CH3:17])[CH3:16])=[O:27])[NH:22][C:23]=1[CH2:24][CH3:25]

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 86648776HCID 86648776, Verbindung

Produkt 1

HCID 86648777tert-Butyl cis(+/-)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-(dimethylamino)-piperidine-1-carboxylateAusbeute 69,4 %

Versuchsvorschrift

The same operation as in Example (196b) was performed using tert-butyl cis(±)-4-amino-3-(dimethylamino)piperidine-1-carboxylate obtained in Example (200c) (93 mg, 0.382 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (1d) (80.1 mg, 0.459 mmol), 1-hydroxybenzotriazole hydrate (77.5 mg, 0.573 mmol), WSC hydrochloride (110 mg, 0.573 mmol) and triethylamine (79.9 μL, 0.573 mmol), to obtain 106 mg of the title compound (69%) as a colorless solid.

Quellen und Nachweise

ORD-Eintrag
ord-0489dccb589f429d97b4a98be74ae641
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927588B2

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