Toluene → HCID 86641343, compound

HRID 1693304Notes

Reaction equation

HRID 1693304 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([CH2:10][N:11]2[N:39]=[C:15]3[CH2:16][C:17](=O)[C:18]4[CH2:19][S:20][N:21]=[C:22]([N:23]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:13]([C:14]=43)=[N:12]2)[C:4]=1[CH3:40].C1(P(=[CH:60][C:61]([O:63][CH3:64])=[O:62])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[C:34]([O:33][C:31]([N:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:22]1[C:13]2[C:14]3[C:15](=[N:39][N:11]([CH2:10][C:5]4[C:4]([CH3:40])=[C:3]([O:2][CH3:1])[C:8]([CH3:9])=[CH:7][N:6]=4)[N:12]=2)[CH:16]=[C:17]([CH2:60][C:61]([O:63][CH3:64])=[O:62])[C:18]=3[CH2:19][S:20][N:21]=1)=[O:32])([CH3:35])([CH3:36])[CH3:37]

Participants

5

Reactant 3

HCID 1140TolueneHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 67279997HCID 67279997, compound

Product 1

HCID 86641343HCID 86641343, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture composed of di-tert-butyl {2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-8-oxo-2,7,8,9-tetrahydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-4-yl}imidodicarbonate of Example 40 (752 mg), methyl triphenylphosphanylideneacetate (617 mg) and toluene (14 ml) was heated with stirring at 60° C. for 10 hours. Ethyl acetate was added to the reaction mixture, followed by washing with water. Then, the organic layer was dried over sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (ethyl acetate-chloroform) to obtain the title compound (275 mg, 33%) as an oil.

Workup

  1. temperaturewas heated
  2. washby washing with water
  3. dry with materialThen, the organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe concentrated residue was purified by silica gel column chromatography (ethyl acetate-chloroform)

Sources & evidence

ORD record
ord-6a93103d71b04610b038d906a3977594
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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