Trifluoroacetic acid → 3,4-Didehydronaratriptan

HRID 1028420Notes

Reaction equation

HRID 1028420 reaction equation
[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2)(=[O:5])=[O:4].[CH3:17][N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(O)C>[CH3:1][NH:2][S:3]([CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[C:21]1[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][CH:20]=1)(=[O:5])=[O:4]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 740491-Methyl-4-piperidoneHCID 516892Sodium BicarbonateHCID 134757652-(1H-Indol-5-yl)-N-methylethane-1-sulfonamide

Product 1

HCID 200667343,4-Didehydronaratriptan

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
40 °C

Procedure

2-(1H-indol-5-yl)-ethanesulfonic acid methylamide (100 g) was dissolved in ethanol (1000 ml) and N-methyl-4-piperidone (200 ml) was added thereto at 25° C. and a solution of trifluoroacetic acid in ethanol (10 ml in 100 ml) was added over a period of 1 hour. The reaction mass was refluxed for 18-24 hours and cooled to 40° C. The reaction mass was concentrated under vacuum to obtain a residue and water (1500 ml) was added. The mixture was cooled to 10-15° C. and pH of the reaction mass was adjusted to 8 using 5% sodium bicarbonate solution and stirred. The resulting solid was filtered and dried at 50-55° C. under vacuum to obtain title compound (Yield: 93 g, HPLC Purity: 99%)

Workup

  1. temperatureThe reaction mass was refluxed for 18-24 hours
  2. concentrationThe reaction mass was concentrated under vacuum
  3. customto obtain a residue and water (1500 ml)
  4. additionwas added
  5. temperatureThe mixture was cooled to 10-15° C.
  6. filtrationThe resulting solid was filtered
  7. customdried at 50-55° C. under vacuum

Sources & evidence

ORD record
ord-fe0f2be251494dadb3ab22f2d8b1f10e
Source dataset
uspto-grants-2014_05
Patent number
US08735589B2

Reaction notes

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