Ethyl orthoformate → HCID 178482106, compound

HRID 1595408Notes

Reaction equation

HRID 1595408 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=3)=[N:10][C:9]=2[C:23]([NH:25][C:26]2[S:27][CH:28]=[CH:29][N:30]=2)=[O:24])=[CH:4][CH:3]=1.[CH:31](OCC)(OCC)OCC>>[C:19]([C:16]1[CH:15]=[CH:14][C:13]([C:11]2[NH:12][C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][CH3:31])=[CH:7][CH:6]=3)=[C:9]([C:23]([NH:25][C:26]3[S:27][CH:28]=[CH:29][N:30]=3)=[O:24])[N:10]=2)=[CH:18][CH:17]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 178440776HCID 178440776, compound

Product 1

HCID 178482106HCID 178482106, compound

Procedure

5-(4-Aminophenyl)-2-(4-tert-butylphenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide (0.5 g) obtained in Example 77 was refluxed in triethyl orthoformate overnight and concentrated. Thereto were added ethanol and tetrahydrof uran, and sodium borohydride (0.4 g) was added. The mixture was refluxed under heating for 2 hr. After refluxing, water was added and the mixture was extracted with ethyl acetate. The ethyl acetate phase was washed with saturated brine and dried. After drying, the residue was concentrated to give 2-(4-tert-butylphenyl)-5-(4-methylaminophenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide (0.5 g). This was converted to hydrochloride to give 2-(4-tert-butylphenyl)-5-(4-methylaminophenyl)-N-(2-thiazolyl) imidazole-4-carboxamide hydrochloride (0.24 g), melting point 257-259° C. (decomposition).

Workup

  1. concentrationconcentrated
  2. additionThereto were added ethanol and tetrahydrof uran, and sodium borohydride (0.4 g)
  3. additionwas added
  4. temperatureThe mixture was refluxed
  5. temperatureunder heating for 2 hr
  6. temperatureAfter refluxing
  7. additionwater was added
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe ethyl acetate phase was washed with saturated brine
  10. customdried
  11. customAfter drying
  12. concentrationthe residue was concentrated

Sources & evidence

ORD record
ord-6086442f3cdd4d5a9f08c674436f037d
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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