Hydrochloric Acid → HCID 22674069, compound

HRID 1005697Notes

Reaction equation

HRID 1005697 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[Br:12].FC(F)(F)C([N:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][C:21]([S:27](Cl)(=[O:29])=[O:28])=[CH:22][CH:23]=2)[CH2:18]1)=O.[OH-].[Na+].Cl.[CH2:36]([OH:38])[CH3:37]>>[Br:12][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[N:4]=[CH:3][C:2]([N:1]([C:36](=[O:38])[CH3:37])[S:27]([C:21]1[CH:20]=[C:19]3[C:24]([CH2:25][CH2:26][NH:17][CH2:18]3)=[CH:23][CH:22]=1)(=[O:28])=[O:29])=[CH:11]2

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 113249022-(Trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chlorideHCID 226741618-Bromoquinolin-3-amine

Product 1

HCID 22674069HCID 22674069, compound

Procedure

White crystals (180 mg) were obtained in the same manner as in Example 1, except using 145 mg (0.65 mmol) of 3-amino-8-bromoquinoline (Preparation Example 5) and 277 mg (0.85 mmol) of 1,2,3,4-tetrahydro-2-(trifluoroacetyl)isoquinoline-7-sulfonyl chloride. To the crystals were added ethanol (20 ml) and 1 N sodium hydroxide aqueous solution (0.5 ml), followed by stirring at room temperature for 30 minutes. To the reaction mixture was added 1 N hydrochloric acid (0.4 ml), followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated. To the resulting residue were added pyridine (0.5 ml) and acetic anhydride (0.014 ml), followed by stirring at room temperature for 1 hour. Brine was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by silica gel chromatography, to give 113 mg of the title compound.

Workup

  1. extractionby extracting with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. additionTo the resulting residue were added pyridine (0.5 ml) and acetic anhydride (0.014 ml)
  6. stirringby stirring at room temperature for 1 hour
  7. additionBrine was added
  8. extractionthe mixture was extracted with ethyl acetate
  9. dry with materialThe organic layer was dried over magnesium sulfate
  10. concentrationconcentrated
  11. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-745db91c5cbe48a9a5d1e368e477d489
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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