HCID 10505011, compound → HCID 10050798, compound

HRID 1003213Notes

Reaction equation

HRID 1003213 reaction equation
[CH2:1]([N:3]([CH2:6][C:7]1[N:12]=[C:11]2[S:13][C:14]3[CH2:15][NH:16][CH2:17][CH2:18][C:19]=3[C:10]2=[C:9]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[C:8]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:4][CH3:5])[CH3:2]>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[CH2:4]([N:3]([CH2:6][C:7]1[N:12]=[C:11]2[S:13][C:14]3[C:19]([C:10]2=[C:9]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[C:8]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:18][CH:17]=[N:16][CH:15]=3)[CH2:1][CH3:2])[CH3:5]

Participants

4

Reactant 1

HCID 10505011HCID 10505011, compound

Product 1

HCID 10050798HCID 10050798, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of the compound obtained in Example 5A (10.16 g), activated manganese dioxide (30.93 g) and toluene (200 ml) was stirred under refluxing conditions for 11.5 hours. The reaction mixture was filtered; the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane-methanol (20:20:1, v/v) to yield ethyl 2-(N,N-diethylaminomethyl)-4-(3,4-dimethoxyphenyl)thieno[2,3-b:5,4-c']dipyridine-3-carboxylate (for structural formula, see below) (3.1 g, 31%), which was then recrystallized from ethyl acetate to yield colorless needle crystals having a melting point of 163 to 165° C. ##STR47##

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washeluted with ethyl acetate-hexane-methanol (20:20:1

Sources & evidence

ORD record
ord-b7afb58d911b421b914314c9d3c3b8b3
Source dataset
uspto-grants-2000_04
Patent number
US06046189

Reaction notes

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