HCID 10063214, compound → HCID 454825, compound

HRID 1033011Notes

Reaction equation

HRID 1033011 reaction equation
C[O:2][C:3]1[C:8]([CH2:9][NH:10][C:11]2[O:12][C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[N:15]=2)=[CH:7][C:6]([CH2:20][CH3:21])=[C:5]([CH3:22])[N:4]=1.Cl.N1C=CC=CC=1>O>[O:12]1[C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=[C:11]1[NH:10][CH2:9][C:8]1[C:3](=[O:2])[NH:4][C:5]([CH3:22])=[C:6]([CH2:20][CH3:21])[CH:7]=1

Participants

4

Reactant 2

HCID 10063214HCID 10063214, compoundHCID 10176127Pyridinium chloride

Product 1

HCID 454825HCID 454825, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-methoxy-3-{[(benzoxazol-2-yl)amino]methyl}-5-ethyl-6-methylpyridine (80 mg, 0.269 mmol) and pyridine hydrochloride (335 mg, 2.9 mmol), under a nitrogen atmosphere, was warmed in an oil bath pre-heated to 150° C. for 5 minutes. This solidified mixture was cooled, diluted with water and the crude precipitated product collected by filtration. This material was dissolved in methylene chloride, filtered through a charcoal pad and then diluted with hexane. As the methylene chloride was boiled off the product crystallized out to give 40 mg (53%), m.p. 211°-213° C.

Workup

  1. temperatureunder a nitrogen atmosphere, was warmed in an oil bath
  2. temperatureThis solidified mixture was cooled
  3. customthe crude precipitated product
  4. filtrationcollected by filtration
  5. dissolutionThis material was dissolved in methylene chloride
  6. filtrationfiltered through a charcoal pad
  7. additiondiluted with hexane
  8. customcrystallized out
  9. customto give 40 mg (53%), m.p. 211°-213° C.

Sources & evidence

ORD record
ord-1a7400ffeab449cdb7091da15d4b34f1
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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