Pyridine → HCID 178474103, compound

HRID 1595401Notes

Reaction equation

HRID 1595401 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](C)=[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.[C:28](Cl)(=[O:30])[CH3:29].N1C=CC=C[CH:33]=1>>[C:28]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH3:33])=[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)(=[O:30])[CH3:29]

Participants

4

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 178424019HCID 178424019, compound

Product 1

HCID 178474103HCID 178474103, compound

Procedure

2-(4-Aminophenyl)-5-(4-methylphenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide (0.30 g) obtained in Example 21 was dissolved in pyridine (20 ml) and acetyl chloride (0.8 ml) was added dropwise under ice-cooling. The mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated to give white crystals, which were recrystallized from ethyl acetate to give 2-(4-acetamidophenyl)-5-(methylphenyl)-N-(2-thiazolyl)imidazole-4-carboxamide (0.17 g), melting point 269-271° C.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. customto give white crystals, which
  4. customwere recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-2d33c90ce2c14b3bad5ea7228b124924
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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