HCID 22350183, compound → HCID 22350203, compound

HRID 902138Notes

Reaction equation

HRID 902138 reaction equation
[NH:1]1[C:12]2[C:4](=[CH:5][CH:6]=[C:7]3[C:11]=2[CH:10]=[CH:9][NH:8]3)[CH:3]=[C:2]1[C:13]([O:15]C)=[O:14].C[Si](C)(C)[O-].[K+]>O1CCCC1>[NH:1]1[C:12]2[C:4](=[CH:5][CH:6]=[C:7]3[C:11]=2[CH:10]=[CH:9][NH:8]3)[CH:3]=[C:2]1[C:13]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 22350183HCID 22350183, compoundHCID 23668039Potassium trimethylsilanolate2×

Product 1

HCID 22350203HCID 22350203, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.53 g (2.5 mmol) of methyl 1,6-dihydro-1,6-diaza-as-indacene-2-carboxylate, 0.36 g (2.5 mmol) of potassium trimethylsilanolate (Aldrich) and 6.0 ml of tetrahydrofuran is refluxed for 1 h, further 0.18 g (1.25 mmol) of potassium trimethylsilanolate is added and after 5 h reflux the reaction mixture is concentrated. The residue is mixed with 20 ml of water, the undissolved material is filtered off, 0.32 ml of hydrochloric acid is added to the filtrate, the precipitated crude product is filtered off and purified by column chromatography using Kieselgel 60 (Merck) as adsorbent, and chloroform:methanol=9:1 as eluent. The product is crystallized with diethyl ether to yield 0.22 g (44%) of the title compound. Mp.: 248-250° C. (diethyl ether).

Workup

  1. temperatureis refluxed for 1 h
  2. temperaturereflux the reaction mixture
  3. concentrationis concentrated
  4. additionThe residue is mixed with 20 ml of water
  5. filtrationthe undissolved material is filtered off
  6. addition0.32 ml of hydrochloric acid is added to the filtrate
  7. customthe precipitated crude product
  8. filtrationis filtered off
  9. custompurified by column chromatography
  10. customThe product is crystallized with diethyl ether

Sources & evidence

ORD record
ord-fcc834005f8f4aafb034e2e983c9ca3c
Source dataset
uspto-grants-2008_04
Patent number
US07365083B2

Reaction notes

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