Trifluoroacetic acid → HCID 86707270, compound

HRID 576052Notes

Reaction equation

HRID 576052 reaction equation
FC(F)(F)C(O)=O.COC1C=C(OC)C=CC=1C[N:13]([C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=2)=[CH:35][C:34]=1[F:48])[S:14]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[CH2:23][N:22]([C:27](=[O:32])[C:28]([F:31])([F:30])[F:29])[CH2:21][CH2:20]2)(=[O:16])=[O:15].C(=O)([O-])O.[Na+]>C1(OC)C=CC=CC=1.C(Cl)(Cl)Cl>[F:48][C:34]1[CH:35]=[C:36]([O:39][CH2:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=2)[CH:37]=[CH:38][C:33]=1[NH:13][S:14]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[CH2:23][N:22]([C:27](=[O:32])[C:28]([F:29])([F:31])[F:30])[CH2:21][CH2:20]2)(=[O:15])=[O:16]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86707271HCID 86707271, compound

Product 1

HCID 86707270HCID 86707270, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (1 mL) was added to a solution of N-(2,4-dimethoxybenzyl)-N-{2-fluoro-4-[2-(pyridin-2-yl)ethoxy]phenyl}-2-(trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-6-sulfonamide obtained (350 mg) in a mixture of anisole (5 mL) and chloroform (5 mL) while cooling in ice, and the mixture was stirred at room temperature for 16 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution while cooling in ice, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and 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 (hexane:ethyl acetate=70:30→chloroform:methanol=95:5) to afford N-{2-fluoro-4-[2-(pyridin-2-yl)ethoxy]phenyl}-2-(trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-6-sulfonamide as a colorless oil (12 mg).

Workup

  1. customobtained (350 mg)
  2. temperaturewhile cooling in ice
  3. temperaturewhile cooling in ice
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried 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 (hexane:ethyl acetate=70:30→chloroform:methanol=95:5)

Sources & evidence

ORD record
ord-4c30079a3a7d469a9fef4169b4bcaa49
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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