1-Hydroxybenzotriazole → 4-Chloro-2-[(cyclopropylmethyl)aminocarbonyl]pyridine

HRID 387926

Reaktionsgleichung

Reaktionsgleichung von HRID 387926
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=O)[CH:3]=1.Cl.[NH2:12][CH2:13][CH:14]1[CH2:16][CH2:15]1.Cl.C(N=C=NCCCN(CC)CC)C.ON1C2C=CC=CC=2N=N1>O.O1CCCC1.C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:12][CH2:13][CH:14]2[CH2:16][CH2:15]2)=[O:10])[CH:3]=1

Komponenten

8

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 81671(Cyclopropylmethyl)ammonium chlorideHCID 2308904-Chloropyridine-2-carboxylic acidHCID 99645121-(3-Diethylaminopropyl)-3-ethylcarbodiimide hydrochloride

Produkt 1

HCID 348291214-Chloro-2-[(cyclopropylmethyl)aminocarbonyl]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

4-Chloro-2-carboxypyridine (2.0 g), (aminomethyl)cyclopropane hydrochloride (1.7 g), 1-ethyl-3-(3-diethylaminopropyl)carbodiimide hydrochloride (WSC) (2.9 g), 1-hydroxybenzotriazole (HOBt) (2.3 g), triethylamine (2.1 ml) and tetrahydrofuran (30 ml) were stirred together at room temperature for 2 hours. Water was added, extraction was performed with ethyl acetate, and then silica gel was added to the extract and the solvent was distilled off under reduced pressure. The silica gel was charged into a dry column packed with silica gel and purified by column chromatography (hexane:ethyl acetate=4:1, followed by 2:1) to obtain 1.5 mg of the target substance as a yellow oil.

Aufarbeitung

  1. extractionextraction
  2. additionsilica gel was added to the
  3. extractionextract
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionThe silica gel was charged into a dry column
  6. custompurified by column chromatography (hexane:ethyl acetate=4:1, followed by 2:1)
  7. customto obtain 1.5 mg of the target substance as a yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-b268e0e64c834e73af0da496495d3866
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372981B2

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