Sulfuric acid magnesium salt (1:1) → HCID 87424661, compound

HRID 2408489Notes

Reaction equation

HRID 2408489 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][N:4]=1.[CH3:11][C:12]([S@:15]([NH2:17])=[O:16])([CH3:14])[CH3:13].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)(Cl)Cl.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6](/[CH:7]=[N:17]/[S@@:15]([C:12]([CH3:14])([CH3:13])[CH3:11])=[O:16])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 33645766-Methoxypyridine-3-carbaldehydeHCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 87424661HCID 87424661, compound

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
65 °C

Procedure

6-Methoxynicotinaldehyde, (a-1), (20.0 g, 146 mmol) and (R)-(+)-2-methyl-2-propanesulfinamide, (a-2), (21.2 g, 175 mmol) were dissolved in chloroform (140 mL) and PPTS (1.8 g, 7.3 mmol), magnesium sulfate (17.6 g, 146 mmol) and copper(II)sulfate (46.6 g, 292 mmol) were added. The mixture was heated to 65° C. overnight. The material was allowed to cool and was filtered through a Solka Floc pad and concentrated under vacuum. The material was purified by flash chromatography on silica gel gradient eluted with 0-40% EtOAc in hexane affording the product (1-A). HPLC/MS: 241.0 (M+1); Rt=2.84 min.

Workup

  1. temperatureto cool
  2. filtrationwas filtered through a Solka Floc pad
  3. concentrationconcentrated under vacuum
  4. customThe material was purified by flash chromatography on silica gel gradient
  5. washeluted with 0-40% EtOAc in hexane affording the product (1-A)

Sources & evidence

ORD record
ord-6a62949b839143eba816ee356a25cdc5
Source dataset
uspto-grants-2014_08
Patent number
US08815865B2

Reaction notes

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