1-(1-(6-Chloro-3-((1-(quinolin-2-yl)azetidin-3-yl)oxy)pyridazin-4-yl)piperidin-4-yl)ethanone → 1-(1-(3-((1-(Quinolin-2-yl)azetidin-3-yl)oxy)pyridazin-4-yl)piperidin-4-yl)ethanone

HRID 454942Notes

Reaction equation

HRID 454942 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([O:8][CH:9]2[CH2:12][N:11]([C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[CH2:10]2)=[C:4]([N:23]2[CH2:28][CH2:27][CH:26]([C:29](=[O:31])[CH3:30])[CH2:25][CH2:24]2)[CH:3]=1>CO.[Pd]>[N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[N:11]1[CH2:10][CH:9]([O:8][C:5]2[N:6]=[N:7][CH:2]=[CH:3][C:4]=2[N:23]2[CH2:24][CH2:25][CH:26]([C:29](=[O:31])[CH3:30])[CH2:27][CH2:28]2)[CH2:12]1

Participants

4

Reactant 1

HCID 585478521-(1-(6-Chloro-3-((1-(quinolin-2-yl)azetidin-3-yl)oxy)pyridazin-4-yl)piperidin-4-yl)ethanone

Product 1

HCID 585480461-(1-(3-((1-(Quinolin-2-yl)azetidin-3-yl)oxy)pyridazin-4-yl)piperidin-4-yl)ethanoneYield 96.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-(1-(6-chloro-3-((1-(quinolin-2-yl)azetidin-3-yl)oxy)pyridazin-4-yl)piperidin-4-yl)ethanone (1.1 g, 2.6 mmol) and wet Pd—C (50%, 1.0 g) in MeOH (30 mL) was stirred under H2 (40 psi) at room temperature for 1.5 hours then the reaction mixture was filtered through CELITE® and washed with MeOH. The filtrate was concentrated in vacuo to give 1-(1-(3-((1-(quinolin-2-yl)azetidin-3-yl)oxy)pyridazin-4-yl)piperidin-4-yl)ethanone (0.98 g, 2.5 mmol, yield 96%). ESI-MS (M+1): 404 calc. for C24H26N4O2 403.

Workup

  1. filtrationthe reaction mixture was filtered through CELITE®
  2. washwashed with MeOH
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-53c589b751bd4745809bf45c1029c11c
Source dataset
uspto-grants-2013_07
Patent number
US08497265B2

Reaction notes

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