HCID 178522566, compound → HCID 178460432, compound

HRID 1595411Notes

Reaction equation

HRID 1595411 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:13][C:12]([C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:24]([NH:26][C:27]2[S:28][CH:29]=[CH:30][N:31]=2)=[O:25])=[CH:5][CH:4]=1>N1C=CC=CC=1.C(OC(=O)CC)(=O)CC>[C:14]1([C:12]2[NH:13][C:9]([C:6]3[CH:5]=[CH:4][C:3]([CH2:2][O:1][C:2](=[O:1])[CH2:3][CH3:4])=[CH:8][CH:7]=3)=[C:10]([C:24]([NH:26][C:27]3[S:28][CH:29]=[CH:30][N:31]=3)=[O:25])[N:11]=2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 178522566HCID 178522566, compound

Product 1

HCID 178460432HCID 178460432, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 31263Propionic anhydrideSolvent

Procedure

5-(4-Hydroxymethylphenyl)-2-(1-naphthyl)-N-(2-thiazolyl)-imidazole-4-carboxamide (300 mg) obtained in Example 61 was dissolved in pyridine (5 ml) and propionic anhydride (5 ml), and the mixture was left standingfor 12 hr. Thereaction mixture was poured into icewater and extracted with ethyl acetate. The ethyl acetate layer was washed with water and, after drying, concentrated. The obtained residue was recrystallized from ethyl acetate to give 2-(1-naphthyl)-5-(4-propionyloxymethylphenyl)-N-(2-thiazolyl)imidazole-4-carboxamide (150 mg), melting point 281-283° C.

Workup

  1. additionThereaction mixture was poured into icewater
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. customafter drying
  5. concentrationconcentrated
  6. customThe obtained residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a04abff03bed4301b2e4b3a19412ea82
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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