Methanol → HCID 68443794, compound

HRID 1814138Notes

Reaction equation

HRID 1814138 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2C3=N[CH:13]=[C:14]([S:16][CH3:17])[N:15]=[C:10]3[CH:9]=[C:8]2[CH:18]=[O:19])=[CH:4][CH:3]=1.[C-:22]#[N:23].[Na+].[CH3:25][OH:26]>[O-2].[O-2].[Mn+4]>[CH3:25][O:26][C:18]([C:8]1[N:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:21][CH:20]=2)[C:22]2=[N:23][CH:13]=[C:14]([S:16][CH3:17])[N:15]=[C:10]2[CH:9]=1)=[O:19]

Participants

5

Reactant 3

HCID 887MethanolHCID 8929Sodium CyanideHCID 22504428HCID 22504428, compound

Product 1

HCID 68443794HCID 68443794, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Conditions

Temperature
22.5 °C

Procedure

To the compound obtained in Example 34 (6) (15 mg), methanol (2.8 ml), manganese dioxide (22 mg) and sodium cyanide (13 mg) were added at 0° C. and the mixture was stirred at 15 to 30° C. for 15 hours. The reaction solution was then filtered through Celite, extracted with chloroform, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was separated using silica gel preparative thin-layer chromatography (chloroform:methanol=100:1) to obtain 11 mg (66.4%) of the desired product as a white powder.

Workup

  1. filtrationThe reaction solution was then filtered through Celite
  2. extractionextracted with chloroform
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was separated

Sources & evidence

ORD record
ord-fdda87c636ed444f96684fcd8f99583b
Source dataset
uspto-grants-2005_04
Patent number
US06875770B2

Reaction notes

Loading…