Sumatriptan → HCID 19816150, compound

HRID 2248012Notes

Reaction equation

HRID 2248012 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14][S:15]([NH:18][CH3:19])(=[O:17])=[O:16])[CH:12]=2)[NH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+]>FC(F)(F)C(O)=O>[CH3:20][N:2]([CH3:1])[CH2:3][CH2:4][CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14][S:15]([NH:18][CH3:19])(=[O:16])=[O:17])[CH:12]=2)[NH:7][CH2:6]1

Participants

4

Reactant 2

HCID 5358SumatriptanHCID 11430Potassium Carbonate

Product 1

HCID 19816150HCID 19816150, compoundYield 15.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a suspension of 3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulphonamide (0.5 g) in trifluoroacetic acid (15 ml) at -10° was added borane-tetrahydrofuran complex (45 ml; 1M) keeping the temperature below +2°. The resulting suspension was stirred at 0° for 5 min, poured onto saturated potassium carbonate (50 ml) and extracted with ethanol (2×20 ml). The ethanolic extract was evaporated and the residue purified by column chromatography (A) to give the title compound as an oil (80 mg). T.l.c. (N), Rf 0.53 (IPA, CeIV).

Workup

  1. additionwas added borane-tetrahydrofuran complex (45 ml; 1M)
  2. customthe temperature below +2°
  3. extractionextracted with ethanol (2×20 ml)
  4. extractionThe ethanolic extract
  5. customwas evaporated
  6. customthe residue purified by column chromatography (A)

Sources & evidence

ORD record
ord-1dd108e31aa847959da8bf845a8e04a8
Source dataset
uspto-grants-1991_08
Patent number
US05037845

Reaction notes

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