2-(2-Acetamidophenyl)acetic acid → 8-(2-Acetaminobenzyl)-3-(2-phenylethyl)-1-propylxanthine

HRID 29876Notes

Reaction equation

HRID 29876 reaction equation
[NH:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12](O)=O)[C:2]([CH3:4])=[O:3].[NH2:15][C:16]1[C:17](=[O:35])[N:18]([CH2:32][CH2:33][CH3:34])[C:19](=[O:31])[N:20]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:21]=1[NH2:22]>>[NH:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]1[NH:15][C:16]2[C:17](=[O:35])[N:18]([CH2:32][CH2:33][CH3:34])[C:19](=[O:31])[N:20]([CH2:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:21]=2[N:22]=1)[C:2]([CH3:4])=[O:3]

Participants

3

Reactant 2

HCID 146221782-(2-Acetamidophenyl)acetic acidHCID 184495295,6-Diamino-1-(2-phenylethyl)-3-propyluracil

Product 1

HCID 184495348-(2-Acetaminobenzyl)-3-(2-phenylethyl)-1-propylxanthine

Procedure

By the method of Example 2, 2-(acetamino)phenylacetic acid is reacted with 5,6-diamino-1-(2-phenylethyl)-3-propyluracil to yield 8-(2-acetaminobenzyl)-3-(2-phenylethyl)-1-propylxanthine. By methods well known in the art, 8-(2-acetaminobenzyl)-3-(2-phenylethyl)-1-propylxanthine is hydrolyzed with base to yield 8-(2-aminobenzyl)-3-(2-phenylethyl)-1-propylxanthine. In turn, 5,6-diamino-1-(2-(phenylethyl)-3-propyluracil is made by the synthetic methods of Example 1, starting with phenethylamine hydrochloride.

Sources & evidence

ORD record
ord-182d68a5bfe24aaea0895aa1aeb431d7
Source dataset
uspto-grants-2008_09
Patent number
US07423041B2

Reaction notes

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