Methanesulfonic Acid → Nanterinone mesylate

HRID 1199522Notes

Reaction equation

HRID 1199522 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:13]2[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]2[CH3:19])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[CH:7]2.[CH3:20][S:21]([OH:24])(=[O:23])=[O:22].C(OCC)(=O)C>CO>[CH3:20][S:21]([OH:24])(=[O:23])=[O:22].[CH3:1][C:2]1[CH:3]=[C:4]([N:13]2[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]2[CH3:19])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8857Ethyl AcetateHCID 71305Nanterinone

Product 1

HCID 92089Nanterinone mesylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of 8-methyl-6-(2,4-dimethylimidazol-1-yl)-2-(1H)-quinolone (365.7 g) in methanol (914 cm3) at 60° was treated with methanesulphonic acid (141.9 g) over 5 minutes. Ethyl acetate (3.4 l) was added and the solution was allowed to cool to room temperature for 1 hour followed by cooling in an ice bath for 2 hours. The solid was filtered off, washed with ethyl acetate (450 cm3) and dried in vacuo at 50° to afford the title compound, m.p. 282°-284°.

Workup

  1. temperatureby cooling in an ice bath for 2 hours
  2. filtrationThe solid was filtered off
  3. washwashed with ethyl acetate (450 cm3)
  4. customdried in vacuo at 50°

Sources & evidence

ORD record
ord-00e58a1cc7b1450f9a607421c373d92b
Source dataset
uspto-grants-1990_02
Patent number
US04900839

Reaction notes

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