Trifluoroacetic acid → HCID 25062517, compound

HRID 1787772Notes

Reaction equation

HRID 1787772 reaction equation
COC1C=CC(C[N:8]2[C:16]3[C:15](=[O:17])[N:14]4[C:18]([CH3:21])=[N:19][N:20]=[C:13]4[N:12]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:11]=3[N:10]=[C:9]2[S:27][CH3:28])=CC=1.FC(F)(F)C(O)=O>>[CH3:21][C:18]1[N:14]2[C:15](=[O:17])[C:16]3[NH:8][C:9]([S:27][CH3:28])=[N:10][C:11]=3[N:12]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:13]2=[N:20][N:19]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57600173HCID 57600173, compound

Product 1

HCID 25062517HCID 25062517, compoundYield 42%

Procedure

A solution of 6-(4-methoxybenzyl)-3-methyl-7-(methylthio)-9-pentyl-6,9-dihydro-5h-[1,2,4]triazolo[4,3-a]purin-5-one (200 mg, 469 mmol) in trifluoroacetic acid (5 ml, 64.9 mmol) was stirred at 55° C. overnight. The solution was concentrated and purified by prep LCMS to yield the desired product (60 mg, 42%). 1HNMR (300 MHz, CD3OD): δ 4.42 (t, J=7.5 Hz, 2H), 2.74 (s, 3H), 2.45 (s, 3H), 1.92 (m, 2H), 1.39 (m, 4H), 0.92 (m, 3H). LCMS calculated for C13H19N6OS(M+H): 307.1; found 307.1.

Workup

  1. concentrationThe solution was concentrated
  2. custompurified by prep LCMS

Sources & evidence

ORD record
ord-31c63bfb65b549b3bab6aaaa47aade52
Source dataset
uspto-grants-2009_03
Patent number
US07511050B2

Reaction notes

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