HCID 59402704, compound → HCID 59402815, compound

HRID 415572Notes

Reaction equation

HRID 415572 reaction equation
[CH2:1](N)[CH2:2]N.[C-]#[C-].[Li+].[Li+].Br[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]([C:24]([NH2:26])=[O:25])[CH:21]=[CH:22][CH:23]=1>CS(C)=O.Cl>[CH2:16]([O:17][C:18]1[CH:19]=[C:20]([C:24]([NH2:26])=[O:25])[CH:21]=[CH:22][CH:23]=1)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:1]#[CH:2]

Participants

5

Reactant 2

HCID 59402704HCID 59402704, compoundHCID 178511344HCID 178511344, compound

Product 1

HCID 59402815HCID 59402815, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

(Method F) Lithium acetylide ethylenediamine complex (305 mg, 3.3 mmol, 1.1 equiv.) was placed in a three-neck flask, degassed, flushed with N2 and suspended in DMSO (2 ml). To the stirred suspension a solution of 3-[(7-bromoheptyl)oxy]benzenecarboxamide (943 mg, 3 mmol, 1 equiv.) in DMSO (2 ml), was added, slowly, dropwise, at r.t., under N2. The reaction mixture was stirred at r.t. for 16 h. After that time it was diluted with 1N HCl solution and extracted with EtOAc (×3). The combined organic extracts were washed with brine, dried (Na2SO4) and evaporated to dryness under reduced pressure. The crude product was purified by column chromatography on silica eluting with EtOAc/hexane 20%, to give the desired compound as a white solid (100 mg, 13%), mp 82-83° C. HPLC-MS (method 1): m/z 260 [M+H]+, Rt=4.26 min.

Workup

  1. customdegassed
  2. customflushed with N2
  3. customat r.t.
  4. extractionextracted with EtOAc (×3)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated to dryness under reduced pressure
  8. customThe crude product was purified by column chromatography on silica eluting with EtOAc/hexane 20%

Sources & evidence

ORD record
ord-96c57823b09740ee8ff7c988750df4a6
Source dataset
uspto-grants-2012_01
Patent number
US08088791B2

Reaction notes

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