HCID 67059728, compound → HCID 67059738, compound

HRID 1671287Notes

Reaction equation

HRID 1671287 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:9][N:10]2[C:13]2[S:14][CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>CO.[C].[Pd]>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[N:9][N:10]2[C:13]2[S:14][CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 67059728HCID 67059728, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67059738HCID 67059738, compoundYield 18.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

10% Palladium-carbon (18 mg, manufactured by Merck Chemicals, Ltd.) was added to a solution of ethyl 2-(6-nitro-3-phenyl-1H-indazol-1-yl)thiazole-4-carboxylate (234 mg), which had been synthesized from the compound of Reference Example 24 according to the method of Example 3, in methanol (20 mL manufactured by Wako Pure Chemical Industries, Ltd.) at room temperature, and the mixture was stirred overnight in a hydrogen atmosphere. After completion of the reaction, the 10% palladium-carbon was removed by filtration, and the solvent was evaporated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:4), to give 39.1 mg of the title compound. LC-MS: HPLC retention time 1.95 minutes, m/z 365 (M+H), condition C-1.

Workup

  1. customAfter completion of the reaction
  2. customthe 10% palladium-carbon was removed by filtration
  3. customthe solvent was evaporated
  4. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:4)

Sources & evidence

ORD record
ord-a9b22f85cebd4d48b51be596d5dd818b
Source dataset
uspto-grants-2011_08
Patent number
US07994202B2

Reaction notes

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