HCID 25121885, compound → HCID 178438004, compound

HRID 2194629Notes

Reaction equation

HRID 2194629 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][CH:26]=1)[CH2:6][C:7]1[O:11][C:10]([NH:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][N:17]=[C:16]3[CH:22]=[CH2:23])=[N:9][N:8]=1>CO.[Pd]>[CH2:22]([C:16]1[C:15]2[C:19](=[CH:20][CH:21]=[C:13]([NH:12][C:10]3[O:11][C:7]([CH2:6][C:5]4[CH:24]=[CH:25][CH:26]=[C:3]([O:2][CH3:1])[CH:4]=4)=[N:8][N:9]=3)[CH:14]=2)[NH:18][N:17]=1)[CH3:23]

Participants

4

Reactant 1

HCID 25121885HCID 25121885, compound

Product 1

HCID 178438004HCID 178438004, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

150 mg of [5-(3-methoxybenzyl)-1,3,4-oxadiazol-2-yl]-(3-vinyl-1H-indazol-5-yl)amine (as trifluoroacetic acid salt, prepared from “A43”) are hydrogenated at room temperature in 10 ml of methanol in the presence of 150 mg of Pd/C. The reaction mixture is filtered and evaporated. Purification by column chromatography on silica gel (eluent: heptane/EA) gives 50 mg of (3-ethyl-1H-indazol-5-yl)-[5-(3-methoxybenzyl)-1,3,4-oxadiazol-2-yl]amine (44%); MS-FAB (M+H+)=350.39; Rf (polar method): 1.836 min.;

Workup

  1. filtrationThe reaction mixture is filtered
  2. customevaporated
  3. customPurification by column chromatography on silica gel (eluent: heptane/EA)

Sources & evidence

ORD record
ord-3d26f9b387e8465fb1232a5c56b30ccc
Source dataset
uspto-grants-2012_12
Patent number
US08334309B2

Reaction notes

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