Methanol → HCID 178489030, compound

HRID 1595418Notes

Reaction equation

HRID 1595418 reaction equation
O.[ClH:2].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:15][C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[CH:17]=3)=[N:13][C:12]=2[C:25]([NH:27][C:28]2[S:29][CH:30]=[CH:31][N:32]=2)=[O:26])=[CH:7][CH:6]=1.CO>[C].[Pd].O1CCOCC1>[ClH:2].[NH2:22][C:18]1[CH:17]=[C:16]([C:14]2[NH:15][C:11]([C:8]3[CH:9]=[CH:10][C:5]([O:4][CH3:3])=[CH:6][CH:7]=3)=[C:12]([C:25]([NH:27][C:28]3[S:29][CH:30]=[CH:31][N:32]=3)=[O:26])[N:13]=2)[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 178489033HCID 178489033, compound

Product 1

HCID 178489030HCID 178489030, compoundYield 12.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

5-(4-Methoxyphenyl)-2-(3-nitrophenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide hydrochloride monohydrate (1.0 g) was suspended in a mixed solvent of methanol (100 ml) and dioxane (100 ml), and 10% palladium carbon (containing water 50%, 0.5 g) was added to carryoutcatalyticreductionatnormalpressure. Thereactionmixture was filtered and concentrated. The obtained crude crystals were recrystallized from methanol to give 2-(3-aminophenyl)-5-(4-methoxyphenyl)-N-(2-thiazolyl)imidazole-4-carboxamide hydrochloride 3/2 hydrate (110 mg), melting point 245° C. (decomposition).

Workup

  1. additionwas added to carryoutcatalyticreductionatnormalpressure
  2. filtrationThereactionmixture was filtered
  3. concentrationconcentrated
  4. customThe obtained crude crystals
  5. customwere recrystallized from methanol

Sources & evidence

ORD record
ord-033bf46a9da24e999d17db08cc41aa53
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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