3,6-Dichloropyridazine → HCID 178482152, Verbindung

HRID 1743766Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1743766
[CH3:1][NH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]#[C:10][CH2:11][OH:12])[CH2:5][CH2:4]1.[Cl:13][C:14]1[N:15]=[N:16][C:17](Cl)=[CH:18][CH:19]=1.C(N(C(C)C)C(C)C)C>CN(C=O)C>[Cl:13][C:14]1[N:15]=[N:16][C:17]([N:2]([CH3:1])[C@H:3]2[CH2:4][CH2:5][C@H:6]([C:9]#[C:10][CH2:11][OH:12])[CH2:7][CH2:8]2)=[CH:18][CH:19]=1

Komponenten

5

Edukt 3

HCID 673313,6-DichloropyridazineHCID 81531DiisopropylethylamineHCID 178484802HCID 178484802, Verbindung

Produkt 1

HCID 178482152HCID 178482152, VerbindungAusbeute 54,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 0.67 g (4 mmol) trans-3-(4-Methylamino-cyclohexyl)-prop-2-yn-1-ol, 2.76 g (18 mmol) of 3,6-dichloropyridazine and 1.76 ml (13.6 mmol) N-ethyldiisopropylamine was heated for 3.5 h at 80° C., diluted with 1 ml DMF and heated for 4 days at 80° C. and one day at 120° C. The reaction was cooled, evaporated and partitioned between aqueous saturated NaHCO3/Et2O (3×). The organic phases were washed with aqueous 10% NaCl, dried (NaSO4) and evaporated. Flash chromatography on silica gel (MeCl2/Et2O 95:5 to 9:1) gave 0.61 g (54%) of trans-3-{4-[(6-Chloro-pyridazin-3-yl)-methyl-amino]-cyclohexyl}-prop-2-yn-1-ol, MS: 280 (MH+, 1Cl).

Aufarbeitung

  1. temperatureheated for 4 days at 80° C. and one day at 120° C
  2. temperatureThe reaction was cooled
  3. customevaporated
  4. custompartitioned between aqueous saturated NaHCO3/Et2O (3×)
  5. washThe organic phases were washed with aqueous 10% NaCl
  6. dry with materialdried (NaSO4)
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-1c85958104564df7b0089956576fc4b1
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07012077B2

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