Dimethylformamide → Acetate hexane

HRID 325094Notes

Reaction equation

HRID 325094 reaction equation
Cl.NC1N2N=C(C3[O:13][CH:14]=[CH:15]C=3)N=C2C=C(N2CCNCC2)N=1.[C:23]1(CCBr)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.CN(C=[O:43])C>>[C:14]([O-:43])(=[O:13])[CH3:15].[CH3:27][CH2:28][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7666Phenethyl bromideHCID 8471TriethylamineHCID 220024325-Amino-2-(2-furyl)-7-piperazinyl[1,2,4]triazolo[1,5-c]-pyrimidine hydrochloride

Product 1

HCID 22139250Acetate hexane

Conditions

Temperature
60 °C

Procedure

In 10 ml of DMF, 400 mg (1.04 mmol) of Compound 43 obtained in Example 43 was dissolved, and 0.51 ml (3.6 mmol) of 2-phenylethyl bromide and 1 ml of triethylamine were added thereto, followed by stirring at 60° C. for 2 hours. The reaction mixture was extracted by adding chloroform and water, and the organic phase was dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, the residue was purified by silica gel column chromatography [chloroform-methanol (97:3)] and recrystallized from ethyl. acetate-hexane to give 369 mg (yield: 95%) of Compound 46 as light gray powder.

Workup

  1. extractionThe reaction mixture was extracted
  2. additionby adding chloroform and water
  3. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  4. customAfter evaporation of the solvent under reduced pressure
  5. customthe residue was purified by silica gel column chromatography [chloroform-methanol (97:3)]
  6. customrecrystallized from ethyl

Sources & evidence

ORD record
ord-f8d96c12c1364e309b040b8fbf6bae6f
Source dataset
uspto-grants-2001_04
Patent number
US06222035B1

Reaction notes

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