Benzoyl chloride → HCID 135709009, compound

HRID 382366Notes

Reaction equation

HRID 382366 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][N:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:6]=1[C:7]([NH2:9])=[O:8].C(Cl)(=O)C1C=CC=CC=1.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][C:35](Cl)=O)=[CH:30][CH:29]=1>>[CH2:10]([N:5]1[C:6]2[C:7](=[O:8])[NH:9][C:35]([CH2:34][C:31]3[CH:32]=[CH:33][C:28]([O:27][CH3:26])=[CH:29][CH:30]=3)=[N:1][C:2]=2[N:3]=[CH:4]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 7412Benzoyl chlorideHCID 27346884-Methoxyphenylacetyl chlorideHCID 140006201-benzyl-4-amino-1H-imidazole-5-carboxamide

Product 1

HCID 135709009HCID 135709009, compoundYield 18%

Procedure

An amidation reaction was carried out under the same conditions as in Example 1 using 6.48 g (30 mmol) of 4-amino-1-benzyl-5-imidazole carboxamide obtained in Reference Example 2 and using, instead of benzoyl chloride, 4-methoxyphenylacetyl chloride which was separately prepared according to a conventional method. A crude amide product was obtained after the post-treatment. The crude amide was subjected to a cyclization reaction for 13 hours under the same conditions as in Example 1. 1.92 g of 7-benzyl-2-(4-methoxybenzyl)hypoxanthine was obtained after the post-treatment. Yield 18% (2 steps).

Workup

  1. customAn amidation reaction
  2. customobtained in Reference Example 2
  3. customwas separately prepared
  4. customA crude amide product was obtained after the post-treatment

Sources & evidence

ORD record
ord-08427ab04351470eb3c3b39e79277669
Source dataset
uspto-grants-2001_10
Patent number
US06310070B1

Reaction notes

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