HCID 86625257, compound → HCID 59420876, compound

HRID 499192Notes

Reaction equation

HRID 499192 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH:22]3[CH2:27][CH2:26][N:25](OCC4C=CC=CC=4)[C:24](=C=O)[CH2:23]3)[CH:16]=2)=[O:13])[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[CH:16]=2)=[O:13])[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86625257HCID 86625257, compound

Product 1

HCID 59420876HCID 59420876, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-3-{3-[1-(benzyloxy)-carbonyl-piperidin-4-yloxy]phenyl}urea. (Example 54. below, 6.62 g, 13.1 mmol) and 10% palladium on carbon (1 g) in ethanol (200 mL) is stirred at 22° C. under hydrogen gas for 2.5 hours. The catalyst is removed by filtration. The filtrate is concentrated to give brown oil, which solidifies upon standing at 22° C. over weekend. The residue is purified on a silica gel chromatography by eluting with methanol and dichloromethane. A peach color solid is obtained (3.51 g, 72% yield, ES+(m/z) 372.3 [M+H]).

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationThe filtrate is concentrated
  3. customto give brown oil, which
  4. waitupon standing at 22° C. over weekend
  5. customThe residue is purified on a silica gel chromatography
  6. washby eluting with methanol and dichloromethane
  7. customA peach color solid is obtained (3.51 g, 72% yield, ES+(m/z) 372.3 [M+H])

Sources & evidence

ORD record
ord-b8ac830f819a4722979de8f32455400f
Source dataset
uspto-grants-2010_08
Patent number
US07767674B2

Reaction notes

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