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Triethylamine → 6-(3-(6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-3-yl)piperidin-1-yl)-3-nitropyridin-2-amine

HRID 931130
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 931130
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]2[N:8]3[CH2:14][CH2:13][CH2:12][C:9]3=[N:10][N:11]=2)[CH2:2]1.Cl[C:16]1[N:21]=[C:20]([NH2:22])[C:19]([N+:23]([O-:25])=[O:24])=[CH:18][CH:17]=1.C(N(CC)CC)C>C(#N)C>[N:10]1[N:11]=[C:7]([CH:3]2[CH2:4][CH2:5][CH2:6][N:1]([C:16]3[N:21]=[C:20]([NH2:22])[C:19]([N+:23]([O-:25])=[O:24])=[CH:18][CH:17]=3)[CH2:2]2)[N:8]2[CH2:14][CH2:13][CH2:12][C:9]=12
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Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 431427873-{5H,6H,7H-pyrrolo[2,1-c][1,2,4]triazol-3-yl}piperidine

Produkt 1

HCID 898542026-(3-(6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-3-yl)piperidin-1-yl)-3-nitropyridin-2-amineAusbeute 72,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Versuchsvorschrift

To a solution of 3-(piperidin-3-yl)-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazole (900 mg, 4.68 mmol) in acetonitrile (50 mL) was added 6-chloro-3-nitropyridin-2-amine (730 mg, 4.2 mmol) and triethylamine (1.42 g, 14.04 mmol) at room temperature under a nitrogen atmosphere. The reaction mixture was stirred for 30 min at reflux, then allowed to cool down to room temperature and stirred for 16 h. The solvent was removed under reduced pressure and the resulting residue was partitioned between water and ethyl acetate. The organics were dried over sodium sulfate, concentrated under reduced pressure and purified via column chromatography to afford the title compound (1.0 g, 64.9%). MS (ES+) (M+H) 330.33; LCMS retention time: 2.85 min (Method S).

Aufarbeitung

  1. temperatureat reflux
  2. stirringstirred for 16 h
  3. customThe solvent was removed under reduced pressure
  4. customthe resulting residue was partitioned between water and ethyl acetate
  5. dry with materialThe organics were dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. custompurified via column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-14430e84c40142d799295a3f557a8982
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09296745B2

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