Ammonia → Tert-butyl 4-(4-carbamoyl-2-oxo-2,3-dihydroimidazol-1-yl)piperidine-1-carboxylate

HRID 1867604Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1867604
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[C:17]([C:19]([OH:21])=O)[NH:16][C:15]2=[O:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C[N:25](C)CCCN=C=NCC.O.N1(O)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.N.C(=O)(O)[O-].[Na+]>CN(C)C=O.ClCCl>[NH2:25][C:19]([C:17]1[NH:16][C:15](=[O:22])[N:14]([CH:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:9][CH2:10]2)[CH:18]=1)=[O:21]

Komponenten

9

Edukt 6

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59006370HCID 59006370, Verbindung

Produkt 1

HCID 59006367Tert-butyl 4-(4-carbamoyl-2-oxo-2,3-dihydroimidazol-1-yl)piperidine-1-carboxylateAusbeute 37,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1-[1-(tert-butoxycarbonyl)piperidin-4-yl]-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid (210 mg, 0.675 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (388 mg, 2.02 mmol), 1H-1,2,3-benzotriazol-1-ol hydrate (273 mg, 2.02 mmol), N,N-diisopropylethylamine (0.352 mL, 2.02 mmol), and ammonia (0.5 M, 2.02 mmol, 4.05 mL) were stirred at room temperature in dimethylformamide (10 mL). After 3 h, the reaction was worked up with dichloromethane and saturated sodium bicarbonate. The organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→15% methanol {1% ammonium hydroxide}/dichloromethane) gave the title compound (78 mg). MS 255.2 (M+1-tert butyl)

Aufarbeitung

  1. washThe organic extracts were washed with brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (100% dichloromethane→15% methanol {1% ammonium hydroxide}/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-d0099aa00efa4223bb8d44b767a8e95c
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07632832B2

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