Ethylene Glycol → HCID 21254896, compound

HRID 636446Notes

Reaction equation

HRID 636446 reaction equation
[Na].[C:2]1([S:8]([C:11]2[C:12]([CH2:28][CH3:29])=[N:13][N:14]3[C:19]([N:20]4[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]4)=[CH:18][C:17](Cl)=[N:16][C:15]=23)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:30]([OH:33])[CH2:31][OH:32]>>[C:2]1([S:8]([C:11]2[C:12]([CH2:28][CH3:29])=[N:13][N:14]3[C:19]([N:20]4[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]4)=[CH:18][C:17]([O:32][CH2:31][CH2:30][OH:33])=[N:16][C:15]=23)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 5360545SodiumHCID 21255002HCID 21255002, compound

Product 1

HCID 21254896HCID 21254896, compoundYield 44%

Procedure

0.274 g (12 mmol) of sodium was added to 40 ml of ethylene glycol and this solution was treated with 0.50 g (1.2 mmol) of 3-benzenesulphonyl-5-chloro-2-ethyl-7-(4-methyl-piperazin-1-yl)-pyrazolo[1,5-a]pyrimidine and subsequently stirred at 80° for 1 hr. After cooling to RT the reaction solution was poured on to 70 ml of ice-water and extracted three times with 50 ml of AcOEt. The combined organic phases were dried (MgSO4), filtered and evaporated. Chromatography (SiO2, CH2Cl2/MeOH 9:1) of the residue and crystallization from EtOH yielded 0.24 g (44%) of 2-[3-benzenesulphonyl-2-ethyl-7-(4-methyl-piperazin-1-yl)-pyrazolo[1,5-a]pyrimidin-5-yl-oxy]-ethanol as colorless crystals, m.p. 153-154°.

Workup

  1. extractionextracted three times with 50 ml of AcOEt
  2. dry with materialThe combined organic phases were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customChromatography (SiO2, CH2Cl2/MeOH 9:1) of the residue and crystallization from EtOH

Sources & evidence

ORD record
ord-079b5f582242465dbc58cecda4b09a26
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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