Hydrochloric Acid → HCID 10293123, compound

HRID 1633792Notes

Reaction equation

HRID 1633792 reaction equation
[NH2:1][CH2:2][CH2:3][S:4]([C:6]1[CH:7]=[C:8]([C:20]2[NH:21][CH:22]=[CH:23][CH:24]=2)[C:9]2[C:10](=[O:19])[NH:11][C:12]3[C:17]=2[C:16]=1[C:15]([F:18])=[CH:14][CH:13]=3)=[O:5].[ClH:25]>CN(C=O)C.CO>[ClH:25].[NH2:1][CH2:2][CH2:3][S:4]([C:6]1[CH:7]=[C:8]([C:20]2[NH:21][CH:22]=[CH:23][CH:24]=2)[C:9]2[C:10](=[O:19])[NH:11][C:12]3[C:17]=2[C:16]=1[C:15]([F:18])=[CH:14][CH:13]=3)=[O:5]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 9946036HCID 9946036, compound

Product 1

HCID 10293123HCID 10293123, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(2-amino-ethanesulfinyl)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one (from Example 42 above) (20 mg, 0.06 mmol) in DMF (approximately 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 resulting material was further purified by precipitation out of MeOH/CH2Cl2 (3:1) with excess of pentane to give 5-(2-amino-ethanesulfinyl)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one hydrochloride salt as an orange solid. (Yield 19 mg, 77%).

Workup

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

Sources & evidence

ORD record
ord-440492167f2f49c4b6387e56c35674c2
Source dataset
uspto-grants-2003_01
Patent number
US06504034B2

Reaction notes

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