Hydrogen Bromide → Eletriptan Hydrobromide

HRID 843970Notes

Reaction equation

HRID 843970 reaction equation
[BrH:1].[C:2]1([S:8]([CH2:11][CH2:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[CH:16]3)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[CH2:24][CH2:25]OC>>[BrH:1].[CH3:19][N:18]1[CH2:17][CH2:16][CH2:15][C@@H:24]1[CH2:25][C:16]1[C:15]2[C:19](=[CH:20][CH:21]=[C:13]([CH2:12][CH2:11][S:8]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)(=[O:10])=[O:9])[CH:14]=2)[NH:18][CH:17]=1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 80711,2-DimethoxyethaneHCID 461956503-Dealkyl eletriptan

Product 1

HCID 656631Eletriptan Hydrobromide

Procedure

49% w/w Hydrobromic acid (27.86 ml, 0.25 mol) was added over 1 hour to a stirred solution of 3N-methyl-2(R)-pyrrolidinylmethyl)-5-(2-phenylsulphonylethyl)-1H-indole (92.86 g, 0.24 mol) in 1,2-dimethoxyethane (2.08 l) at about 5° C. The cooling bath was removed and the resulting slurry was allowed to granulate by stirring at room temperature for a further 18 hours. Filtration, followed by washing with 1,2-dimethoxyethane and drying in vacuo, afforded the required product (97.9 g) as a solid, m.p. 150-151° C. Found: C,56.77; H,5.87; N,5.85. C22H26N2O2S; HBr requires C,57.02; H,5.87; N,6.04%.

Workup

  1. customThe cooling bath was removed
  2. filtrationFiltration
  3. washby washing with 1,2-dimethoxyethane
  4. customdrying in vacuo

Sources & evidence

ORD record
ord-ea992b9a109d43f28ca3c1021b1c2f81
Source dataset
uspto-grants-2002_04
Patent number
US06380226B1

Reaction notes

Loading…