Pyridine → HCID 54396594, compound

HRID 1199420Notes

Reaction equation

HRID 1199420 reaction equation
[CH3:1][C:2]1([CH3:17])[O:14][C:6]2=[CH:7][C:8]3[C:9]([CH:13]=[C:5]2[CH:4](N)[CH:3]1[OH:16])=[N:10][O:11][N:12]=3.[F:18][C:19]([F:24])([F:23])[C:20](O)=[O:21].[N:25]1C=CC=CC=1>>[CH3:1][C:2]1([CH3:17])[O:14][C:6]2=[C:7]([NH2:25])[C:8]3[C:9]([CH:13]=[C:5]2[CH:4]([C:20](=[O:21])[C:19]([F:24])([F:23])[F:18])[CH:3]1[OH:16])=[N:10][O:11][N:12]=3

Participants

4

Reactant 3

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 11107308(+)-7,8-dihydro-6,6-dimethyl-7-hydroxy-8-amino-6H-pyrano[2,3-f]benz-2,1,3-oxadiazole

Product 1

HCID 54396594HCID 54396594, compoundYield 29%

Conditions

Temperature
0 °C

Procedure

A mixture of 300 mg (1.28 m mol) of 7,8-dihydro-6,6-dimethyl-7-hydroxy-8-amino-6H-pyrano [2,3-f] benzo-2,1,3-oxadiazole and 3 ml of pyridine were added with 180 μl (1.28 m mol) of anhydrous trifluoroacetic acid with stirring for 3 hours at 0° C., followed by further stirring for 3 hours at the room temperature. After the completion of the reaction, the mixture was washed thrice with water and dried over anhydrous sodium sulfate. After the solvent was distilled off, the residue was subjected to a silica gel column chromatography using a developing solvent of ethyl acetate-methanol (10:1 (v/v)) to obtain 124 mg (yield: 29%) of the intended compound. A part of the obtained compound was recrystallized from ethanol to obtain the pure intended compound.

Workup

  1. stirringby further stirring for 3 hours at the room temperature
  2. customAfter the completion of the reaction
  3. washthe mixture was washed thrice with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationAfter the solvent was distilled off

Sources & evidence

ORD record
ord-b3b9bd76c1804775b4e6dcf9315fb39b
Source dataset
uspto-grants-1990_02
Patent number
US04900752

Reaction notes

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