6-[4-[4-(Benzyloxy)phenoxy]piperidin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine → 4-[[1-[3-(Trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]oxy]phenol

HRID 1675057ノート

反応式

HRID 1675057 の反応式
C([O:8][C:9]1[CH:34]=[CH:33][C:12]([O:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:21]=[CH:22][C:23]4[N:24]([C:26]([C:29]([F:32])([F:31])[F:30])=[N:27][N:28]=4)[N:25]=3)[CH2:16][CH2:15]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].CO>[F:32][C:29]([F:30])([F:31])[C:26]1[N:24]2[N:25]=[C:20]([N:17]3[CH2:16][CH2:15][CH:14]([O:13][C:12]4[CH:33]=[CH:34][C:9]([OH:8])=[CH:10][CH:11]=4)[CH2:19][CH2:18]3)[CH:21]=[CH:22][C:23]2=[N:28][N:27]=1

参加物

4

反応物 1

HCID 673399206-[4-[4-(Benzyloxy)phenoxy]piperidin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine

生成物 1

HCID 673407954-[[1-[3-(Trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]oxy]phenol収率 86.1%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

10% Palladium on carbon (0.574 g, 0.54 mmol) was added to 6-[4-[4-(benzyloxy)phenoxy]piperidin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (2.53 g, 5.39 mmol) in MeOH (30 mL) under an atmosphere of hydrogen. The resulting suspension was stirred at ambient temperature for 24 hours. The reaction mixture was evaporated. The crude product was purified by flash silica chromatography, elution gradient 0 to 3% MeOH in DCM. Pure fractions were evaporated to dryness to afford 4-[[1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]oxy]phenol (1.760 g, 86%) as a gum which crystallised on standing.

後処理

  1. customThe reaction mixture was evaporated
  2. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 3% MeOH in DCM
  3. customPure fractions were evaporated to dryness

出典と根拠

ORDレコード
ord-98db2e60edc243f4b8cbad6b6b0d09fb
出典データセット
uspto-grants-2011_08
特許番号
US08003649B2

反応ノート

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