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

HRID 1678747Notes

Reaction equation

HRID 1678747 reaction equation
[CH3:1][C:2]([S:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[C:8]1([C:14]2[C:15]([C:27]3[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=3)=[N:16][C:17]3[CH:18]=[CH:19][N:20]4[CH:26]=[N:25][N:24]=[C:21]4[C:22]=3[CH:23]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(Cl)Cl>[CH3:1][C:2]([S:5](/[N:7]=[CH:31]/[C:30]1[CH:33]=[CH:34][C:27]([C:15]2[C:14]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:23][C:22]3[C:21]4=[N:24][N:25]=[CH:26][N:20]4[CH:19]=[CH:18][C:17]=3[N:16]=2)=[CH:28][CH:29]=1)=[O:6])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 594729044-(9-Phenyl[1,2,4]triazolo[3,4-f][1,6]naphthyridin-8-yl)benzaldehyde

Product 1

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-sulfinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Racemic 2-methyl-2-propane-sulfinamide (7-1, 647 mg, 5.3 mmol), cupric sulfate (1.70 g, 7.30 mmol), and aldehyde 4-2 (511 mg, 1.45 mmol) were stirred in methylene chloride (10 mL) for 5 d at 50° C. After cooling to rt, the mixture was filtered through celite, concentrated to a minimum volume and purified via automated silica gel chromatography (0-10% MeOH in CH2Cl2 over 30 min) to give the title compound as a brown foam. LRMS m/z (M+1) Calcd: 454.2. Found 454.2

Workup

  1. filtrationthe mixture was filtered through celite
  2. concentrationconcentrated to a minimum volume
  3. custompurified
  4. customsilica gel chromatography (0-10% MeOH in CH2Cl2 over 30 min)

Sources & evidence

ORD record
ord-45f5e8c5469d4f9499402a62b63c9901
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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