Sulfuric acid magnesium salt (1:1) → HCID 178434623, compound

HRID 558270Notes

Reaction equation

HRID 558270 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[N:2].[NH2:11][CH2:12][C:13]1[NH:17][N:16]=[C:15]([CH3:18])[C:14]=1[O:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([Cl:28])[CH:27]=1)[C:23]#[N:24].S([O-])([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>CO.ClCCl>[Cl:28][C:26]1[CH:25]=[C:22]([CH:21]=[C:20]([O:19][C:14]2[C:15]([CH3:18])=[N:16][NH:17][C:13]=2[CH2:12][NH:11][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH:27]=1)[C:23]#[N:24]

Participants

7

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 660424-CyanobenzaldehydeHCID 4311764Sodium borohydrideHCID 178434621HCID 178434621, compound

Product 1

HCID 178434623HCID 178434623, compoundYield 20.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-cyanobenzaldehyde (60 mg, 0.460 mmol), the amine of Example 77 (120 mg, 0.460 mmol), magnesium sulphate (500 mg) and dichloromethane (5 ml) was stirred under nitrogen at room temperature for 3 days. The mixture was concentrated under reduced pressure and the crude product was purified by flash column chromatography on silica gel eluting with methanol:ethyl acetate (5:95, by volume) to provide a foam. The foam was dissolved in methanol (5 ml), sodium borohydride (50 mg, 1.31 mmol) was added in one portion at room temperature and the reaction was stirred for 30 minutes. The mixture was concentrated under reduced pressure and the residue was dissolved in dichloromethane (20 ml). The resulting solution was washed with 1M aqueous sodium carbonate solution (10 ml) and brine (10 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:4:1, by volume) to provide the title compound (35 mg) as a white foam.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe crude product was purified by flash column chromatography on silica gel eluting with methanol:ethyl acetate (5:95, by volume)
  3. customto provide a foam
  4. concentrationThe mixture was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in dichloromethane (20 ml)
  6. washThe resulting solution was washed with 1M aqueous sodium carbonate solution (10 ml) and brine (10 ml)
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:4:1, by volume)

Sources & evidence

ORD record
ord-2f67637d04eb4876a472bd0756264bac
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

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