Methanol → HCID 10475538, compound

HRID 2229419Notes

Reaction equation

HRID 2229419 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[O:22][CH:21]=[N:20][CH:19]=3)=[C:14]([O:23][CH3:24])[CH:13]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.[N-:25]([C:28]#[N:29])[C:26]#[N:27].[Na+].CO>CN(C=O)C>[NH2:29][C:28](=[N:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[O:22][CH:21]=[N:20][CH:19]=3)=[C:14]([O:23][CH3:24])[CH:13]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1)[NH:25][C:26]#[N:27]

Participants

5

Reactant 3

HCID 887MethanolHCID 4350929Sodium dicyanamideHCID 15462734HCID 15462734, compound

Product 1

HCID 10475538HCID 10475538, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of 50 mg (0.15 mmol) of 49B in 1 ml of DMF was added excess HCl—ether. A precipitate was obtained. Stirring was continued for 0.5 hr and the slurry was then evaporated to dryness. The residue was diluted with 2 ml of DMF and 40 mg (0.45 mmol) of sodium dicyanamide added. The reaction was heated at 50° C. for 3 hr during which time a lightly cloudy, pale yellow solution was obtained. After removal of the solvent, the residue was diluted with 3 ml of water and stirred for 1 hr. The insolubles were removed by filtration to give 76 mg of the crude product. This material was dissolved into methanol and absorbed onto approx. 1 g of silica gel and subjected to flash chromatography on a 30 cc column of silica gel. Elution with 5% MeOH-EtOAc afforded 9 mg (0.023 mmol, 15%) of 49C as a pale yellow solid. (M+H)+ 392+.

Workup

  1. customA precipitate was obtained
  2. customthe slurry was then evaporated to dryness
  3. additionadded
  4. customwas obtained
  5. customAfter removal of the solvent
  6. additionthe residue was diluted with 3 ml of water
  7. stirringstirred for 1 hr
  8. customThe insolubles were removed by filtration
  9. customto give 76 mg of the crude product
  10. customabsorbed onto approx. 1 g of silica gel
  11. washElution with 5% MeOH-EtOAc

Sources & evidence

ORD record
ord-6bcf53499ad949b5afdd644bdfba6787
Source dataset
uspto-grants-2002_07
Patent number
US06420403B1

Reaction notes

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