Hydrochloric Acid → HCID 9947168, compound

HRID 1633790Notes

Reaction equation

HRID 1633790 reaction equation
[NH2:1][CH2:2][CH2:3][S: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.[ClH:24]>CN(C=O)C.CO>[ClH:24].[NH2:1][CH2:2][CH2:3][S: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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 9858586HCID 9858586, compound

Product 1

HCID 9947168HCID 9947168, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(2-amino-ethylsulfanyl)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one (from Example 40 above) (20 mg, 0.06 mmol) in DMF (2.5 mL) was treated with aqueous HCl with vigorous stirring. The solution was lyophilized and the residue was dissolved in methanol, filtered and concentrated. The residue was further purified by precipitation out of methanol/CH2Cl2 (1:3) with excess pentane to give 5-(2-amino-ethylsulfanyl)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one hydrochloride salt as a dark yellow solid. (Yield 17 mg, 76%).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was further purified by precipitation out of methanol/CH2Cl2 (1:3) with excess pentane

Sources & evidence

ORD record
ord-14531ee69f244b2383e349b8b7cb8c05
Source dataset
uspto-grants-2003_01
Patent number
US06504034B2

Reaction notes

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