Acetic Acid → 6-Methyl-pyridazine-4-carboxylic acid[3-(4-tert-butylcarbamoyl-piperidin-1-ylmethyl)-phenyl]-amide

HRID 1486751Notes

Reaction equation

HRID 1486751 reaction equation
[C:1]([NH:5][C:6]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:16]=[C:17]([NH:21][C:22]([C:24]3[CH:29]=[C:28]([CH3:30])[N:27]=[N:26][C:25]=3Cl)=[O:23])[CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(O)=O>CO.[Pd]>[C:1]([NH:5][C:6]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:16]=[C:17]([NH:21][C:22]([C:24]3[CH:29]=[C:28]([CH3:30])[N:27]=[N:26][CH:25]=3)=[O:23])[CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 1185218653-Chloro-6-methyl-pyridazine-4-carboxylic acid [3-(4-tert-butylcarbamoyl-piperidin-1-ylmethyl)-phenyl]-amide

Product 1

HCID 1185218996-Methyl-pyridazine-4-carboxylic acid[3-(4-tert-butylcarbamoyl-piperidin-1-ylmethyl)-phenyl]-amide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-chloro-6-methyl-pyridazine-4-carboxylic acid [3-(4-tert-butylcarbamoyl-piperidin-1-ylmethyl)-phenyl]-amide (53 mg, 0.119 mmol) in methanol (5 mL) is treated with palladium 10 wt % on activated carbon wet (50% water) (5.1 mg, 0.048 mmol, 0.4 eq) and AcOH (0.00683 ml, 0.119 mmol). The mixture is stirred under hydrogen atmosphere for 4 h. The suspension is filtered over celite and the solvent is evaporated. The residue is purified by prep HPLC E delivering the title compound (7 mg, 14%) as a light yellowish powder, LC-MS A: tR=0.58 min; [M+H]+=410.4.

Workup

  1. filtrationThe suspension is filtered over celite
  2. customthe solvent is evaporated
  3. customThe residue is purified by prep HPLC E

Sources & evidence

ORD record
ord-e746cfb92db14e05b42ec377d98650eb
Source dataset
uspto-grants-2016_08
Patent number
US09428456B2

Reaction notes

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