Triethylamine → HCID 178523782, Verbindung

HRID 724274Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 724274
S(O)(=O)(=O)C.[CH2:6]([O:13][C:14]([C@H:16]1[CH2:21][CH2:20][C@@H:19]([NH2:22])[CH2:18][CH2:17]1)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.[F:30][C:31]1[CH:32]=[N:33][C:34]([Cl:40])=[C:35]([CH:39]=1)[C:36](O)=[O:37].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[CH2:6]([O:13][C:14]([C@H:16]1[CH2:21][CH2:20][C@@H:19]([NH:22][C:36]([C:35]2[C:34]([Cl:40])=[N:33][CH:32]=[C:31]([F:30])[CH:39]=2)=[O:37])[CH2:18][CH2:17]1)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 114352432-Chloro-5-fluoronicotinic acidHCID 178505346HCID 178505346, Verbindung

Produkt 1

HCID 178523782HCID 178523782, VerbindungAusbeute 41,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

cis-4-Amino-cyclohexanecarboxylic acid benzyl ester mesylate (5.34 g, 13.2 mmol) was dissolved in dimethylformamide (75 ml) and triethylamine (5.5 ml, 39.5 mmol) was added followed by 5-fluoro-2-chloronicotinic acid (2.31 g, 13.2 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.77 g, 14.5 mmol) and 1-hydroxybenzotriazole (1.96 g, 14.5 mmol). The reaction was stirred under nitrogen at room temperature for 18 h and the solvent was removed under reduced pressure. The residue was partitioned between sat. sodium bicarbonate solution (50 ml) and ethyl acetate (75 ml) and the aqueous phase was extracted with ethyl acetate (2×75 ml). The combined organic extracts were washed with water (2×20 ml), brine (20 ml), dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with ethyl acetate:pentane (1:1, by volume) to give cis-4-[(2-Chloro-5-fluoro-pyridine-3-carbonyl)-amino]-cyclohexanecarboxylic acid benzyl ester (2.14 g) as a white solid.

Aufarbeitung

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between sat. sodium bicarbonate solution (50 ml) and ethyl acetate (75 ml)
  3. extractionthe aqueous phase was extracted with ethyl acetate (2×75 ml)
  4. washThe combined organic extracts were washed with water (2×20 ml), brine (20 ml)
  5. dry with materialdried over MgSO4
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel eluting with ethyl acetate:pentane (1:1, by volume)

Quellen und Nachweise

ORD-Eintrag
ord-210f75bd82884e45af7e01a8ac15dc38
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141586B2

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