(NE)-2-methyl-N-[[4-(9-phenyl-[1,2,4]triazolo[3,4-f][1,6]naphthyridin-8-yl)phenyl]methylidene]propane-2-sulfinamide → 2-Methyl-N-{1-[4-(9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]ethyl}propane-2-sulfinamide

HRID 1678748Notes

Reaction equation

HRID 1678748 reaction equation
[CH3:1][Mg]Br.[CH3:4][C:5]([S:8](/[N:10]=[CH:11]/[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:26][C:25]3[C:24]4=[N:34][N:35]=[CH:36][N:23]4[CH:22]=[CH:21][C:20]=3[N:19]=2)=[CH:14][CH:13]=1)=[O:9])([CH3:7])[CH3:6]>C(Cl)Cl>[CH3:7][C:5]([S:8]([NH:10][CH:11]([C:12]1[CH:13]=[CH:14][C:15]([C:18]2[C:27]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:26][C:25]3[C:24]4=[N:34][N:35]=[CH:36][N:23]4[CH:22]=[CH:21][C:20]=3[N:19]=2)=[CH:16][CH:17]=1)[CH3:1])=[O:9])([CH3:4])[CH3:6]

Participants

4

Reactant 2

HCID 59472989(NE)-2-methyl-N-[[4-(9-phenyl-[1,2,4]triazolo[3,4-f][1,6]naphthyridin-8-yl)phenyl]methylidene]propane-2-sulfinamideHCID 178418573HCID 178418573, compound

Product 1

HCID 594730512-Methyl-N-{1-[4-(9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]ethyl}propane-2-sulfinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methylmagnesium bromide solution (13.5 mL of 1.4 M solution in 3:1 toluene/THF, 19 mmol) was added to a stirred solution of 2-methyl-N-{(1E)-[4-(9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methylidene}propane-2-sulfinamide (7-2, 298 mg, 0.66 mmol) in methylene chloride (5 mL) at −78° C. and the solution was warmed to rt. After 18 h, the reaction was quenched with saturated ammonium chloride solution and extracted with ethyl acetate, washed with brine, dried over magnesium sulfate, filtered, and concentrated to give an amber foam, which was purified via silica gel chromatography (0-10% MeOH/CH2Cl2 over 30 min) to give the title compound as a yellow foam.

Workup

  1. customthe reaction was quenched with saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an amber foam, which
  8. customwas purified via silica gel chromatography (0-10% MeOH/CH2Cl2 over 30 min)

Sources & evidence

ORD record
ord-a94fbe355a0444b2a9ca0eecc7310a91
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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