2,5-Dimethoxytetrahydrofuran → HCID 22609336, compound

HRID 2306572Notes

Reaction equation

HRID 2306572 reaction equation
[NH2:1][C:2]1[N:6]2[C:7]3[C:12]([C:13](=[O:22])[N:14]([CH2:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:5]2=[N:4][N:3]=1)=[CH:11][C:10]([Br:23])=[CH:9][CH:8]=3.CO[CH:26]1[CH2:30][CH2:29][CH:28](OC)O1>C(O)(=O)C>[CH2:15]([N:14]1[C:13](=[O:22])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:23])[CH:11]=2)[N:6]2[C:2]([N:1]3[CH:26]=[CH:30][CH:29]=[CH:28]3)=[N:3][N:4]=[C:5]12)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 22609464HCID 22609464, compound2×

Product 1

HCID 22609336HCID 22609336, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a 25 ml balloon flask, we resuspend 0.7 g (1.8 mmol) of 1-amino-4-benzyl-7-bromo-4H-[1,2,4]triazolo[4,3-a]quinazolin-5-one (intermediate 10 compound of example 271) in 5 ml of acetic acid. We add 0.25 g (1.9 mmol) of 2.5-dimethoxytetrahydrofuran then heat the mixture by reflux for 1 hour. After cooling down and evaporation of acetic acid under vacuum, we obtain 0.8 g of highly colored solid which is purified by chromatography on silica column by elution with the mixture CH2Cl2/CH3OH (99,4/0,6 then 99/1). The solid obtained from pure fractions is recrystallized in ethanol to give 0.45 g of compound from example 217.

Workup

  1. customIn a 25 ml balloon flask, we resuspend
  2. temperaturethen heat the mixture
  3. temperatureby reflux for 1 hour
  4. temperatureAfter cooling down
  5. customevaporation of acetic acid under vacuum, we
  6. customobtain 0.8 g of highly colored solid which
  7. customis purified by chromatography on silica column by elution with the mixture CH2Cl2/CH3OH (99,4/0,6
  8. customThe solid obtained from pure fractions
  9. customis recrystallized in ethanol

Sources & evidence

ORD record
ord-2202a3fb5ba140eba08463db7d839808
Source dataset
uspto-grants-2004_12
Patent number
US06828315B1

Reaction notes

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