HCID 86761113, compound → HCID 59304444, compound

HRID 2239857Notes

Reaction equation

HRID 2239857 reaction equation
OC(C(F)(F)F)=O.Cl[C:9]1[CH:10]=[C:11]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26]([C:28]3[C:29](=[O:41])[N:30]([C:34]4[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=4)[CH:31]=[CH:32][CH:33]=3)=[O:27])=[CH:21][CH:20]=2)[C:12]2[N:13]([CH:15]=[CH:16][N:17]=2)[N:14]=1.[H][H]>C(N(CC)CC)C.[Pd].CCO>[F:40][C:37]1[CH:38]=[CH:39][C:34]([N:30]2[CH2:31][CH2:32][CH2:33][CH:28]([C:26]([NH:25][C:22]3[CH:21]=[CH:20][C:19]([NH:18][C:11]4[C:12]5[N:13]([CH:15]=[CH:16][N:17]=5)[N:14]=[CH:9][CH:10]=4)=[CH:24][CH:23]=3)=[O:27])[C:29]2=[O:41])=[CH:35][CH:36]=1

Participants

6

Reactant 2

HCID 86761113HCID 86761113, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59304444HCID 59304444, compoundYield 66.7%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of N-(4-((6-chloroimidazo[1,2-b]pyridazin-8-yl)amino)phenyl)-1-(4-fluorophenyl)-2-oxo-1,2-dihydro-3-pyridinecarboxamide TFA salt (0.013 g, 0.027 mmol) from Example XXI(i) and EtOH (4 mL) in a 500 ml PARR bottle was added 10% Pd/C (20 mg) and 2 drops of triethylamine. The PARR bottle was then charged with Hydrogen gas at 55 psi and allow to shake at room temperature for 12 hours. The reaction mixture was then filtered and the filtrate concentrated in vacuo. The residue was purified by preparative HPLC to furnish 0.008 g of the title compound as a TFA salt. LC/MS, m/e 445 (M+1). HPLC Rt, 1.81 mm. YMC ODSC18 column (4.6×50 mm). 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B=0, final % B=100, gradient time 4 mm, hold at 100% B 1 mm, flow rate 4 mL/min.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-629af5fe654f4409acfcd8470e8d5cef
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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