HCID 67976371, compound → HCID 67975881, compound

HRID 706710Notes

Reaction equation

HRID 706710 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:39]=[CH:40][CH:41]=1)[CH2:12][N:13]1[C:21]2[C:16](=[C:17]([NH:22][C:23]([C:25]3[N:29]4[CH:30]=[CH:31][C:32]([O:34][CH2:35][CH2:36][O:37][CH3:38])=[CH:33][C:28]4=[N:27][CH:26]=3)=[O:24])[CH:18]=[CH:19][CH:20]=2)[CH:15]=[N:14]1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH:39]=[CH:40][CH:41]=1)[CH2:12][N:13]1[C:21]2[C:16](=[C:17]([NH:22][C:23]([C:25]3[N:29]4[CH:30]=[CH:31][C:32]([O:34][CH2:35][CH2:36][O:37][CH3:38])=[CH:33][C:28]4=[N:27][CH:26]=3)=[O:24])[CH:18]=[CH:19][CH:20]=2)[CH:15]=[N:14]1

Participants

4

Reactant 1

HCID 67976371HCID 67976371, compound

Product 1

HCID 67975881HCID 67975881, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-(1-(3-(benzyloxy)benzyl)-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide (0.022 g, 0.040 mmol) in MeOH (2 mL) was purged with Argon, treated with 10% palladium on carbon (0.002 g), purged with more Argon, and then attached to a hydrogen balloon. The mixture was stirred at ambient temperature overnight, filtered through glass fiber filter paper, washed with MeOH, concentrated and the residue purified on silica gel (1-3% MeOH in DCM) to provide N-(1-(3-hydroxybenzyl)-1H-indazol-4-yl)-7-(2-methoxyethoxy)imidazo[1,2-a]pyridine-3-carboxamide (0.003 g, 18% yield) as a beige oil. MS (APCI) m/z=458 (M+H).

Workup

  1. custompurged with more Argon
  2. filtrationfiltered through glass fiber
  3. filtrationfilter paper
  4. washwashed with MeOH
  5. concentrationconcentrated
  6. customthe residue purified on silica gel (1-3% MeOH in DCM)

Sources & evidence

ORD record
ord-79799722e6ef4034845fd5930f292a60
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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