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 1675057노트

반응식

HRID 1675057 반응식
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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-98db2e60edc243f4b8cbad6b6b0d09fb
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003649B2

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