Sulfuric acid magnesium salt (1:1) → HCID 21949933, compound

HRID 558284Notes

Reaction equation

HRID 558284 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[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+]>CO.O.ClCCl>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:11][CH2:12][C:13]2[N:17]([CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[N:16]=[C:15]([CH2:28][CH3:29])[C:14]=2[O:30][C:31]2[CH:32]=[C:33]([Cl:38])[CH:34]=[C:35]([Cl:37])[CH:36]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

8

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 660424-CyanobenzaldehydeHCID 4311764Sodium borohydrideHCID 21949757HCID 21949757, compound

Product 1

HCID 21949933HCID 21949933, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-cyanobenzaldehyde (50 mg, 0.380 mmol), the amine of Example 138 (172 mg, 0.400 mmol), magnesium sulphate (200 mg) and dichloromethane (4 ml) was stirred 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) then dichloromethane:methanol (95:5, by volume) to provide the title compound (120 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-d9c90fc3f7444e7ca109022112794982
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

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