N,N-Diethylethylenediamine → (S)-N-[(2-{[2-(diethylamino)ethyl]amino}-2-oxoethyl)(oxo)phenyl-lambda6-sulfanylidene]-5-[(3-hydroxyphenyl)ethynyl]nicotinamide

HRID 391571Notes

Reaction equation

HRID 391571 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:11]=[C:12]([C:16]([N:18]=[S@:19]([CH2:27][C:28]([O:30]CC)=O)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:20])=[O:17])[CH:13]=[N:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:33]([N:35]([CH2:39][CH3:40])[CH2:36][CH2:37][NH2:38])[CH3:34]>CO>[CH2:33]([N:35]([CH2:39][CH3:40])[CH2:36][CH2:37][NH:38][C:28](=[O:30])[CH2:27][S@:19](=[O:20])([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[N:18][C:16](=[O:17])[C:12]1[CH:11]=[C:10]([C:9]#[C:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=2)[CH:15]=[N:14][CH:13]=1)[CH3:34]

Participants

4

Reactant 2

HCID 60993N,N-DiethylethylenediamineHCID 24954917(S)-Ethyl [N-({5-[(3-hydroxyphenyl)ethynyl]pyridin-3-yl}carbonyl)-S-phenylsulfonimidoyl]acetate

Product 1

HCID 24954918(S)-N-[(2-{[2-(diethylamino)ethyl]amino}-2-oxoethyl)(oxo)phenyl-lambda6-sulfanylidene]-5-[(3-hydroxyphenyl)ethynyl]nicotinamideYield 60.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

(S)-Ethyl [N-({5-[(3-hydroxyphenyl)ethynyl]pyridin-3-yl}carbonyl)-S-phenylsulfonimidoyl]acetate (73 mg, 0.16 mmol) in anhydrous MeOH (1.5 mL) was added N,N-diethylethylenediamine (0.12 mL, 0.84 mmol) dropwise. The reaction mixture was heated at 30° C. for 4 hours. The reaction mixture was evaporated and the residue was partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was washed once with brine, dried (anhydrous Na2SO4), concentrated. The residue was purified by chromatography (silica gel, 50:1 CHCl3:MeOH to 10:1 CHCl3:MeOH). The product containing fractions were concentrated to give the title compound as a foamy solid (50 mg, 59%).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was partitioned between EtOAc and saturated aqueous NaHCO3
  3. washThe organic layer was washed once with brine
  4. dry with materialdried (anhydrous Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (silica gel, 50:1 CHCl3:MeOH to 10:1 CHCl3:MeOH)
  7. additionThe product containing fractions
  8. concentrationwere concentrated

Sources & evidence

ORD record
ord-14a1a060f465482fa94ceb1025d891aa
Source dataset
uspto-grants-2013_02
Patent number
US08383825B2

Reaction notes

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