Hydrochloric Acid → HCID 22674069, compound

HRID 1173140Notes

Reaction equation

HRID 1173140 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.[C:36](OC(=O)C)(=[O:38])[CH3:37]>[Cl-].[Na+].O.N1C=CC=CC=1.C(O)C>[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

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 113249022-(Trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chlorideHCID 226741618-Bromoquinolin-3-amine

Product 1

HCID 22674069HCID 22674069, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1049PyridineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

180 mg of white crystals were obtained using 145 mg (0.65 mmol, Production Example 5b) of 3-amino-8-bromoquinoline and 277 mg (0.85 mmol) of 1,2,3,4-tetrahydro-2-(trifluoroacetyl)isoquinoline-7-sulfonyl chloride in the same manner as in Synthetic Example 1b. Ethanol (20 ml) and an aqueous 1 N sodium hydroxide solution (0.5 ml) were added to the crystals, followed by stirring at room temperature for 30 minutes. An aqueous 1 N hydrochloric acid solution (0.4 ml) was added to the reaction solution, followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated, to give the residue. Pyridine (0.5 ml) and acetic acid anhydride (0.014 ml) were added to the residue, followed by stirring at room temperature for one hour. Brine was added thereto, followed by extracting with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated. Then, 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. customto give the residue
  6. stirringby stirring at room temperature for one hour
  7. extractionby extracting with ethyl acetate
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. concentrationconcentrated
  10. customThen, the residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a2cf3dc594a0463f978727b367015248
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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