Sulfuric acid magnesium salt (1:1) → HCID 21949772, compound

HRID 2114647Notes

Reaction equation

HRID 2114647 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[NH2:11][CH2:12][C:13]1[N:17]([CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[N:16]=[C:15]([CH2:28][CH3:29])[C:14]=1[O:30][C:31]1[CH:36]=[C:35]([Cl:37])[CH:34]=[C:33]([Cl:38])[CH:32]=1.S([O-])([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>ClCCl.CO.O>[Cl:38][C:33]1[CH:32]=[C:31]([CH:36]=[C:35]([Cl:37])[CH:34]=1)[O:30][C:14]1[C:15]([CH2:28][CH3:29])=[N:16][N:17]([CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:26])[CH3:24])[C:13]=1[CH2:12][NH:11][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

8

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 312444-MethoxybenzaldehydeHCID 4311764Sodium borohydrideHCID 21949757HCID 21949757, compound

Product 1

HCID 21949772HCID 21949772, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-Methoxybenzaldehyde (46 μl, 0.380 mmol), the amine of Example 138 (172 mg, 0.400 mmol) and magnesium sulphate (200 mg) were stirred in dichloromethane (4 ml) at room temperature for 4 days. The mixture was filtered and the filtrate was concentrated under reduced pressure to leave a yellow oil. The oil was dissolved in methanol (4 ml) and sodium borohydride (18 mg, 0.480 mmol) was added with vigorous stirring. Once the addition was complete the reaction was stirred for 4 hours and then water (2 ml) was added. The mixture was concentrated under reduced pressure and the residue was dissolved in dichloromethane (50 ml). The resulting solution was washed with 1M aqueous potassium carbonate solution (20 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (99:1, by volume) and then dichloromethane:methanol (95:5, by volume) to provide the title compound (142 mg) as a colourless oil.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto leave a yellow oil
  4. additionOnce the addition
  5. concentrationThe mixture was concentrated under reduced pressure
  6. dissolutionthe residue was dissolved in dichloromethane (50 ml)
  7. washThe resulting solution was washed with 1M aqueous potassium carbonate solution (20 ml)
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (99:1, by volume)

Sources & evidence

ORD record
ord-1f47d75cbec64dbca3836b19653e941f
Source dataset
uspto-grants-2008_10
Patent number
US07435728B2

Reaction notes

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