Trifluoroacetic acid → HCID 178482105, compound

HRID 1595417Notes

Reaction equation

HRID 1595417 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[C:11]([C:13]([NH:15][C:16]3[S:17][CH:18]=[CH:19][N:20]=3)=[O:14])[N:12]=2)=[CH:4][CH:3]=1.F[C:30](F)(F)C(O)=O>C([O-])([O-])OCC>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([C:10]2[NH:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][CH3:30])=[CH:3][CH:4]=3)=[N:12][C:11]=2[C:13]([NH:15][C:16]2[S:17][CH:18]=[CH:19][N:20]=2)=[O:14])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178489037HCID 178489037, compound

Product 1

HCID 178482105HCID 178482105, compound

Reagents, catalysts & solvents 1

HCID 53630039EthylorthoformateSolvent

Procedure

To 2-(4-aminophenyl)-5-(4-methoxyphenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide (1.35 g) obtained in Example 48 were added ethyl orthoformate (40 ml) and trifluoroacetic acid (0.5 ml) and the mixture was refluxed under heating for one day. The reaction mixture was concentrated and to the residue were added tetrahydrofuran (40 ml) and ethyl alcohol (25 ml). Sodium borohydride (1.2 g) was added to the mixture with stirring. The mixture was stirred at room temperature for 1 hr and refluxed under heating for 2 hr. The reaction mixture was extracted with ethyl acetate, dried and concentrated. The obtained crude product was purified by silica gel column chromatography to give 5-(4-methoxyphenyl)-2-(4-methylaminophenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide (0.6 g). This compound was dissolved in ethyl acetate and ether—hydrochloric acid was added to allow precipitation of the crystals of hydrochloride. The precipitated crystals were collected by filtration and recrystallized from methyl alcohol to give 5-(4-methoxyphenyl)-2-(4-methylaminophenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide hydrochloride dihydrate (240 mg), melting point 193-197° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for one day
  3. concentrationThe reaction mixture was concentrated and to the residue
  4. additionwere added tetrahydrofuran (40 ml) and ethyl alcohol (25 ml)
  5. additionSodium borohydride (1.2 g) was added to the mixture
  6. stirringThe mixture was stirred at room temperature for 1 hr
  7. temperaturerefluxed
  8. temperatureunder heating for 2 hr
  9. extractionThe reaction mixture was extracted with ethyl acetate
  10. customdried
  11. concentrationconcentrated
  12. customThe obtained crude product
  13. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fa34627a785e4b7f976e3ff765576eba
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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