Trifluoroacetic acid → HCID 86707297, compound

HRID 576089Notes

Reaction equation

HRID 576089 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([N:22]2[CH2:31][CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[C:27]([S:32]([N:35](CC4C=CC(OC)=CC=4OC)[C:36]4[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=4)(=[O:34])=[O:33])[CH:28]=3)[CH2:23]2)([CH3:21])[CH3:20])=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9].C(=O)([O-])O.[Na+]>C1(OC)C=CC=CC=1.C(Cl)(Cl)Cl>[C:8]([C:12]1[CH:13]=[CH:14][C:15]([CH2:18][C:19]([N:22]2[CH2:31][CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[C:27]([S:32]([NH:35][C:36]4[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=4)(=[O:34])=[O:33])[CH:28]=3)[CH2:23]2)([CH3:21])[CH3:20])=[CH:16][CH:17]=1)([CH3:9])([CH3:10])[CH3:11]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86707298HCID 86707298, compound

Product 1

HCID 86707297HCID 86707297, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (0.2 mL) was added to a solution of 2-[1-(4-tert-butylphenyl)-2-methylpropan-2-yl]-N-(2,4-dimethoxybenzyl)-N-(4-fluorophenyl)-1,2,3,4-tetrahydroisoquinoline-6-sulfonamide obtained (22 mg) in a mixture of anisole (1 mL) and chloroform (1 mL) while cooling in ice, and the mixture was stirred for 2.5 hr while cooling in ice. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture while cooling in ice and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and then the desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was purified by NH silica gel column chromatography (chloroform:methanol=49:1) to afford the title compound as a colorless oil (8 mg).

Workup

  1. customobtained (22 mg)
  2. temperaturewhile cooling in ice
  3. temperaturewhile cooling in ice
  4. temperaturewhile cooling in ice
  5. extractionthe mixture was extracted with chloroform
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationthe desiccant was filtered off
  8. concentrationfollowed by concentration under reduced pressure
  9. customThe resulting residue was purified by NH silica gel column chromatography (chloroform:methanol=49:1)

Sources & evidence

ORD record
ord-162037be96cd424798619d7281aef2ea
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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