Water → HCID 66824629, compound

HRID 1468614Notes

Reaction equation

HRID 1468614 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][N:14]2[CH:18]3[N:19]=[C:20]4[C:25]([N:17]3[N:16]([CH3:32])[C:15]2=[O:33])=[C:24]([C:26]2[O:27][CH:28]=[CH:29][CH:30]=2)[N:23]=[CH:22][N:21]4[NH2:31])(=O)=O)=CC=1.[CH3:34][O:35][CH2:36][CH2:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([N:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)=[CH:41][CH:40]=1.CCN(C(C)C)C(C)C.O>CN(C=O)C>[NH2:31][N:21]1[C:20]2[C:25]([N:17]3[N:16]([CH3:32])[C:15](=[O:33])[N:14]([CH2:13][CH2:12][N:48]4[CH2:49][CH2:50][N:45]([C:42]5[CH:41]=[CH:40][C:39]([O:38][CH2:37][CH2:36][O:35][CH3:34])=[CH:44][CH:43]=5)[CH2:46][CH2:47]4)[CH:18]3[N:19]=2)=[C:24]([C:26]2[O:27][CH:28]=[CH:29][CH:30]=2)[N:23]=[CH:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 220249141-[4-(2-Methoxyethoxy)phenyl]piperazineHCID 86696633HCID 86696633, compound

Product 1

HCID 66824629HCID 66824629, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-[5-amino-8-(2-furyl)-1-methyl-2-oxo-[1,2,4]triazolo[5,1-f]purin-3-yl]ethyl 4-methylbenzenesulfonate obtained in step 7 (0.25 g, 0.533 mmol), 1-[4-(2-Methoxy-ethoxy)-phenyl]-piperazine (0.188 g, 0.799 mmol) and DIPEA (0.27 ml, 1.599 mmol) were taken in DMF (5 ml) and stirred at 80° C. for 16 hours. To the reaction mixture water (100 ml) was added and solid obtained was filtered off. The crude product was purified by column chromatography to obtain 5-amino-8-(2-furyl)-3-[2-[4-[4-(2-methoxyethoxy)phenyl]piperazin-1-yl]ethyl]-1-methyl-[1,2,4]triazolo[5,1-f]purin-2-one (0.135 g, 47%) as an off white solid

Workup

  1. customsolid obtained
  2. filtrationwas filtered off
  3. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-5ee07c8d9a83471fa4f65bfd76662f59
Source dataset
uspto-grants-2015_04
Patent number
US09006177B2

Reaction notes

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