Pentanoic Acid → HCID 22100349, compound

HRID 2294889Notes

Reaction equation

HRID 2294889 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[N:4][C:5]([NH2:9])=[C:6]([NH2:8])[CH:7]=1.[C:11](O)(=O)[CH2:12][CH2:13][CH2:14][CH3:15].[OH-].[Na+]>O.C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]2[NH:8][C:11]([CH2:12][CH2:13][CH2:14][CH3:15])=[N:9][C:5]2=[N:4][C:3]=1[CH3:10]

Participants

6

Reactant 3

HCID 7991Pentanoic AcidHCID 14798Sodium HydroxideHCID 1010225-Bromo-6-methyl-2,3-pyridinediamine

Product 1

HCID 22100349HCID 22100349, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

9.0 g (44.6 mmole) of the compound obtained in step 3 and 5.5 g (58 mmole) of valeric acid were mixed with 30 ml of polyphosphoric acid and stirred for 3 hours at 110° C. The reaction solution was dissolved in a mixture of 50 ml of cold water and 50 ml of THF and the resulting solution was neutralized to Ph 8 with cold 40% aqueous NaOH solution with stirring vigorously and extracted with ethyl acetate (50 ml×3). Thereafter, the organic layer was dried over Na2SO4, concentrated under reduced pressure and recrystallized from hexane-methylene chloride to obtain 9.8 g of the title compound (yield 82%).

Workup

  1. stirringwith stirring vigorously
  2. extractionextracted with ethyl acetate (50 ml×3)
  3. dry with materialThereafter, the organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customrecrystallized from hexane-methylene chloride

Sources & evidence

ORD record
ord-c555855ed70e4b9f864052208c885950
Source dataset
uspto-grants-1997_11
Patent number
US05691348

Reaction notes

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