HCID 137328646, compound → HCID 137328645, compound

HRID 1850273Notes

Reaction equation

HRID 1850273 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[N:13]=[N:14][C:15](Cl)=[CH:16][C:17]=2[N:18]2[CH2:23][CH2:22][CH:21]([C:24]([CH3:32])([CH3:31])[O:25][SiH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:20][CH2:19]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([C:12]2[N:13]=[N:14][CH:15]=[CH:16][C:17]=2[N:18]2[CH2:23][CH2:22][CH:21]([C:24]([CH3:32])([CH3:31])[O:25][SiH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:20][CH2:19]2)[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 137328646HCID 137328646, compound

Product 1

HCID 137328645HCID 137328645, compoundYield 92.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-piperidin-1-yl]-6-chloro-pyridazin-3-yl}-azetidine-1-carboxylic acid tert-butyl ester (62) (843 mg, 1.7 mmol) in MeOH was added Pd/C (10%, 0.5 g) under nitrogen. The reaction was stirred under hydrogen at RT for 6 h, filtered to remove Pd/C and concentrated to dryness to give 3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-piperidin-1-yl]-pyridazin-3-yl}-azetidine-1-carboxylic acid tert-butyl ester (63) (730 mg, 1.58 mmol yield 92.9%).

Workup

  1. filtrationfiltered
  2. customto remove Pd/C
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9d650699fa7343d5847160c8f048fef2
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

Loading…