Methanesulfonic Acid → 5-(2-amino-ethoxy)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one methanesulfonic acid salt

HRID 1633773Notes

Reaction equation

HRID 1633773 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:19]2[NH:20][CH:21]=[CH:22][CH:23]=2)[C:8]2[C:9](=[O:18])[NH:10][C:11]3[C:16]=2[C:15]=1[C:14]([F:17])=[CH:13][CH:12]=3.[CH3:24][S:25]([OH:28])(=[O:27])=[O:26]>O1CCOCC1>[CH3:24][S:25]([OH:28])(=[O:27])=[O:26].[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:19]2[NH:20][CH:21]=[CH:22][CH:23]=2)[C:8]2[C:9](=[O:18])[NH:10][C:11]3[C:16]=2[C:15]=1[C:14]([F:17])=[CH:13][CH:12]=3

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 98363415-(2-Amino-ethoxy)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one

Product 1

HCID 186244875-(2-amino-ethoxy)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one methanesulfonic acid salt

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

5-(2-Amino-ethoxy)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one (from Example 19 above) (62.3 mg, 0.20 mmol) was dissolved in hot 1,4-dioxane (2.5 mL) and the solution was filtered through a glass filter. To the clear filtrate was added dropwise a solution of methanesulfonic acid (Aldrich, 16.0 mg, 0.16 mmol) in 1,4-dioxane (0.2 mL) at room temperature and the mixture was stirred for 10 minutes. The precipitate formed was collected and washed with 1,4-dioxane, ether and dried in vacuo to afford 5-(2-amino-ethoxy)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one methanesulfonic acid salt as a yellow solid. (Yield 52.5 mg, 64.5%).

Workup

  1. filtrationthe solution was filtered through a glass
  2. filtrationfilter
  3. customThe precipitate formed
  4. customwas collected
  5. washwashed with 1,4-dioxane, ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-da929dfc346b475189d7e775e1e0c6d7
Source dataset
uspto-grants-2003_01
Patent number
US06504034B2

Reaction notes

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