HCID 178480670, compound → HCID 178480669, compound

HRID 1624967Notes

Reaction equation

HRID 1624967 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:36]=[CH:35][C:11]([CH2:12][NH:13][C:14]([C:16]3[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27]CC5C=CC=CC=5)[CH:22]=4)=[CH:19][NH:18][N:17]=3)=[O:15])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1>CO.[Pd]>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:12][NH:13][C:14]([C:16]3[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=4)=[CH:19][NH:18][N:17]=3)=[O:15])=[CH:35][CH:36]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 178480670HCID 178480670, compound

Product 1

HCID 178480669HCID 178480669, compoundYield 40.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-(3-benzyloxy-phenyl)-1H-pyrazole-3-carboxylic acid 4-(4-methyl-piperazin-1-yl)-benzylamide (25 mg; 0.05 mmol) in methanol (5 ml), was treated with 10% palladium on carbon (10 mg) then hydrogenated at room temperature and pressure overnight. The catalyst was removed by filtration through Celite and the filtrate evaporated. Purification by preparative LC/MS gave 8 mg of the required product as a cream solid. (LC/MS: Rt 1.67 [M+H]+ 392).

Workup

  1. customthen hydrogenated at room temperature
  2. custompressure overnight
  3. customThe catalyst was removed by filtration through Celite
  4. customthe filtrate evaporated
  5. customPurification by preparative LC/MS

Sources & evidence

ORD record
ord-8743c95d5a134536a6acab9e3ec01a19
Source dataset
uspto-grants-2014_07
Patent number
US08779147B2

Reaction notes

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