HCID 59320248, compound → HCID 59320222, compound

HRID 655289Notes

Reaction equation

HRID 655289 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[N:9][C:10]3[C:15]([CH:16]=2)=[CH:14][C:13]([CH2:17][C:18]2[N:22]4[N:23]=[C:24]([CH:27]=[CH2:28])[CH:25]=[CH:26][C:21]4=[N:20][N:19]=2)=[CH:12][CH:11]=3)[CH:4]=[N:3]1>ClCCl.CO.[Pd]>[CH2:27]([C:24]1[CH:25]=[CH:26][C:21]2[N:22]([C:18]([CH2:17][C:13]3[CH:14]=[C:15]4[C:10](=[CH:11][CH:12]=3)[N:9]=[CH:8][C:7]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)=[CH:16]4)=[N:19][N:20]=2)[N:23]=1)[CH3:28]

Participants

5

Reactant 1

HCID 59320248HCID 59320248, compound

Product 1

HCID 59320222HCID 59320222, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(1-methyl-1H-pyrazol-4-yl)-6-(6-vinyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-quinoline (22 mg, 0.06 mmol) in dichloromethane (5 mL) and methanol (0.5 mL) under an atmosphere of N2(g) was added 10% palladium on carbon (20 mg) and the atmosphere replaced with H2(g). After stirring vigorously for 3 hours the mixture was filtered through a pad of celite and purified via flash column chromatography (SiO2, CH2Cl2, methanol 0-10%) to return the title compound as a white solid (17 mg, 77%). Analytical data presented in Table 2.

Workup

  1. filtrationwas filtered through a pad of celite
  2. custompurified via flash column chromatography (SiO2, CH2Cl2, methanol 0-10%)

Sources & evidence

ORD record
ord-3b17cdf71d00479fba2817f98df4dfaa
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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