Triethylamine → 4-(cyclopropoxy)-N-[1-(5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-ylcarbamoyl)cyclopropyl]benzamide

HRID 2068553Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2068553
[CH:1]1[N:5]2[C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[CH2:8][CH2:9][CH:10]([NH2:11])[C:4]2=[N:3][CH:2]=1.[CH:16]1([O:19][C:20]2[CH:34]=[CH:33][C:23]([C:24]([NH:26][C:27]3([C:30](O)=[O:31])[CH2:29][CH2:28]3)=[O:25])=[CH:22][CH:21]=2)[CH2:18][CH2:17]1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl>[CH:16]1([O:19][C:20]2[CH:21]=[CH:22][C:23]([C:24]([NH:26][C:27]3([C:30](=[O:31])[NH:11][CH:10]4[CH2:9][CH2:8][C:7]5[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=5[N:5]5[CH:1]=[CH:2][N:3]=[C:4]45)[CH2:29][CH2:28]3)=[O:25])=[CH:33][CH:34]=2)[CH2:18][CH2:17]1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 583040445,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-amineHCID 672344531-(4-Cyclopropoxybenzamido)cyclopropanecarboxylic acid

Produkt 1

HCID 672348194-(cyclopropoxy)-N-[1-(5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-ylcarbamoyl)cyclopropyl]benzamideAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-amine (400 mg, 2.01 mmol), 1-(4-cyclopropoxybenzamido)cyclopropanecarboxylic acid (577 mg, 2.21 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (462 mg, 2.41 mmol) and 1-hydroxybenzotriazole hydrate (369 mg, 2.41 mmol) in dichloromethane (8 mL), add triethylamine (1.26 mL, 9.03 mmol) and stir the mixture at ambient temperature for approximately 16 hours. Purify the crude mixture by flash chromatography (0% to 5% MeOH/dichloromethane) to give the title compound (791 mg, 89%) as a tan foam: MS (m/z): 443 (M+1).

Aufarbeitung

  1. customPurify the crude mixture by flash chromatography (0% to 5% MeOH/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-ca2191e02ca7434a8ead6138e42ce688
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299061B2

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