HCID 86611737, compound → HCID 68485064, compound

HRID 2239858Notes

Reaction equation

HRID 2239858 reaction equation
Cl[C:2]1[CH:3]=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:14][CH:13]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1>C(N(CC)CC)C.[Pd].CCO>[N:10]1[CH:9]=[CH:8][N:6]2[C:5]=1[C:4]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[CH:16][CH:17]=1)=[CH:3][CH:2]=[N:7]2

Participants

5

Reactant 1

HCID 86611737HCID 86611737, compound

Product 1

HCID 68485064HCID 68485064, compoundYield 93.3%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a mixture of tert-butyl 4-(6-chloroimidazo[1,2-b]pyridazin-8-ylamino)phenylcarbamate (0.1 g, 0.28 mmol) from 1a and EtOH (4 mL) in a 500 ml PARR bottle was added 10% Pd/C (0.02 g) and 2 drops of triethyl amine. The PARR bottle was then charged with H2 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 to give 0.085 g of crude tert-butyl 4-(imidazo[1,2-b]pyridazin-8-ylamino)phenylcarbamate.

Workup

  1. additionThe PARR bottle was then charged with H2 at 55 psi
  2. filtrationThe reaction mixture was then filtered
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-5c1fa821941d41d6bfc6200261b94882
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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