Diisopropylethylamine → 4-Pyridin-3-yl-1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-ol

HRID 1675084

Reaktionsgleichung

Reaktionsgleichung von HRID 1675084
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][N:10]=2)[N:7]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2([OH:27])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH:16]=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2([OH:27])[CH2:22][CH2:23][N:24]([C:2]3[CH:3]=[CH:4][C:5]4[N:6]([C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][N:10]=4)[N:7]=3)[CH2:25][CH2:26]2)[CH:16]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 6136576-Chloro-3-(trifluoromethyl)-(1,2,4)triazolo(4,3-b)pyridazineHCID 49891674-(Pyridin-3-yl)piperidin-4-ol

Produkt 1

HCID 441258304-Pyridin-3-yl-1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-olAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A stirred solution of 6-chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (24.29 g, 109.15 mmol), 4-(pyridin-3-yl)piperidin-4-ol (21.40 g, 120.07 mmol) and DIPEA (24.72 ml, 141.90 mmol) in DMF (95 ml) was heated at 80° C. for 1 hour. The solution was cooled to ambient temperature and slowly diluted with water, with seeding, to give a crystalline precipitate. The precipitate was collected by filtration, washed with water, acetonitrile and ether and dried under vacuum to afford 4-pyridin-3-yl-1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-ol (36.1 g, 91%) as a solid.

Aufarbeitung

  1. customto give a crystalline precipitate
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water, acetonitrile and ether
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f3327dd475dd47d4ae73284718b53d50
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003649B2

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