HCID 66767058, compound → HCID 66767064, compound

HRID 2195514Notes

Reaction equation

HRID 2195514 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[N:18]([CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)[C:19](=[O:21])[CH3:20])[N:14]([CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29]1)[N:13]=[CH:12]2)C1C=CC=CC=1>CCO.CCOC(C)=O.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[N:18]([CH:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1)[C:19](=[O:21])[CH3:20])[N:14]([CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29]1)[N:13]=[CH:12]2

Participants

5

Reactant 1

HCID 66767058HCID 66767058, compound

Product 1

HCID 66767064HCID 66767064, compoundYield 88.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent3×

Procedure

To a solution of N-(5-(benzyloxy)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl)-N-(tetrahydro-2H-pyran-4-yl)acetamide (1.7 g, 3.78 mmol) in EtOH (100 mL) and EtOAc (100 mL) is added Pd/C (1 g, 10% wt). After the reaction mixture is stirred at RT under H2 overnight, it is filtered and the filtrate is concentrated. The residue is purified by silica gel column chromatography eluting first with PE:EtOAc (1:1) and then EtOAc to give the product (1.2 g, 88.2% yield). MS (m/z): 360.2 (M+H).

Workup

  1. filtrationit is filtered
  2. concentrationthe filtrate is concentrated
  3. customThe residue is purified by silica gel column chromatography
  4. washeluting first with PE

Sources & evidence

ORD record
ord-468b50faab504f48b62bfe87f696f4d2
Source dataset
uspto-grants-2012_12
Patent number
USRE043878E1

Reaction notes

Loading…