3-Pyridineacetic acid → N-{4-[3-cyclopropylmethyl-1-(2-fluorobenzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-N-methyl-2-pyridin-3-yl-acetamide

HRID 720659Notes

Reaction equation

HRID 720659 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]([OH:10])=O)[CH:2]=1.[CH:11]1([CH2:14][N:15]2[C:23]3[N:22]=[C:21]([CH2:24][C:25]4[CH:30]=[CH:29][C:28]([NH:31][CH3:32])=[CH:27][CH:26]=4)[NH:20][C:19]=3[C:18](=[O:33])[N:17]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[F:41])[C:16]2=[O:42])[CH2:13][CH2:12]1.C(N(CC)CC)C>>[CH:11]1([CH2:14][N:15]2[C:23]3[N:22]=[C:21]([CH2:24][C:25]4[CH:26]=[CH:27][C:28]([N:31]([CH3:32])[C:8](=[O:10])[CH2:7][C:3]5[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=5)=[CH:29][CH:30]=4)[NH:20][C:19]=3[C:18](=[O:33])[N:17]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[F:41])[C:16]2=[O:42])[CH2:13][CH2:12]1

Participants

4

Reactant 3

HCID 1083-Pyridineacetic acidHCID 8471TriethylamineHCID 218916913-Cyclopropylmethyl-8-[4-(methylamino)-benzyl]-1-(2-fluorobenzyl)-3,7-dihydropurine-2,6-dione

Product 1

HCID 58739229N-{4-[3-cyclopropylmethyl-1-(2-fluorobenzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-N-methyl-2-pyridin-3-yl-acetamide

Procedure

This compound was prepared by a method similar to that described in example 79 except that commercially available 3-pyridylacetic acid was used in place of N-acetyl-6-amino-2-pyridine carboxylic acid, the reaction was performed using 0.69 equivalents of 3-cyclopropylmethyl-8-[4-(methylamino)-benzyl]-1-(2-fluorobenzyl)-3,7-dihydropurine-2,6-dione and 0.78 equivalents of triethylamine was added as the final reagent to the reaction mixture. The product was purified by chromatography using silica gel eluted with 93:7 chloroform/methanol followed by crystallization from acetonitrile. MS, m/z(M+)=553.2364.

Workup

  1. customThis compound was prepared by a method similar to
  2. customThe product was purified by chromatography
  3. washeluted with 93:7 chloroform/methanol
  4. customfollowed by crystallization from acetonitrile

Sources & evidence

ORD record
ord-b004862b9b7b4d70b58fa01a45736090
Source dataset
uspto-grants-2006_11
Patent number
US07135475B2

Reaction notes

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