Potassium Carbonate → Alosetron

HRID 2379160Notes

Reaction equation

HRID 2379160 reaction equation
COC[N:4]1[C:8]([CH3:9])=[C:7]([CH2:10][N:11]2[CH2:24][CH2:23][C:14]3[N:15]([CH3:22])[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[C:13]=3[C:12]2=[O:25])[N:6]=[CH:5]1.COCN1C(CN2CCC3N(C)C4C=CC=CC=4C=3C2=O)=C(C)N=C1.C(=O)([O-])[O-].[K+].[K+]>Br>[CH3:22][N:15]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=2[C:13]2[C:12](=[O:25])[N:11]([CH2:10][C:7]3[N:6]=[CH:5][NH:4][C:8]=3[CH3:9])[CH2:24][CH2:23][C:14]1=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 189577172,3,4,5-tetrahydro-2-[[1-(methoxymethyl)-5-methyl-1H-imidazol-4-yl]methyl]-5-methyl-1H-pyrido[4,3-b]indol-1-oneHCID 189577512,3,4,5-tetrahydro-2-[[1-(methoxymethyl)-4-methyl-1H-imidazol-5-yl]methyl]-5-methyl-1H-pyrido[4,3-b]indol-1-one

Product 1

HCID 2099Alosetron

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 2,3,4,5-tetrahydro-2-[[1-(methoxymethyl)-5-methyl-1H-imidazol-4-yl]methyl]-5-methyl-1H-pyrido[4,3-b]indol-1-one and 2,3,4,5-tetrahydro-2-[[1-(methoxymethyl)-4-methyl-1H-imidazol-5-yl]methyl]-5-methyl-1H-pyrido[4,3-b]indol-1-one (34 mg) in 49% hydrobromic acid (2 ml) was heated on a steam bath for ca. 3 h. After cooling, the reaction mixture was basified by addition of potassium carbonate solution and extracted with ethyl acetate (3×50 ml). The combined, dried organic extracts were concentrated in vacuo to give the title compound (6 mg) as a solid. The 1H-n.m.r. and t.l.c. data obtained for this material were consistent with those obtained for the product of Example 20.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. concentrationdried organic extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-8cd9b819742c496db5648d12aa60346b
Source dataset
uspto-grants-1994_11
Patent number
US05360800

Reaction notes

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