Chloroform → HCID 86707289, compound

HRID 576085Notes

Reaction equation

HRID 576085 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][N:20]2[CH2:29][CH2:28][C:27]3[C:22](=[CH:23][CH:24]=[C:25]([S:30]([N:33](CC4C=CC(OC)=CC=4OC)[C:34]4[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][C:45]5[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=5)=[CH:36][C:35]=4[F:51])(=[O:32])=[O:31])[CH:26]=3)[CH2:21]2)=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9].C(Cl)(Cl)Cl.C(=O)([O-])O.[Na+]>C1(OC)C=CC=CC=1>[C:8]([C:12]1[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][N:20]2[CH2:29][CH2:28][C:27]3[C:22](=[CH:23][CH:24]=[C:25]([S:30]([NH:33][C:34]4[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][C:45]5[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=5)=[CH:36][C:35]=4[F:51])(=[O:31])=[O:32])[CH:26]=3)[CH2:21]2)=[CH:16][CH:17]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86707290HCID 86707290, compound

Product 1

HCID 86707289HCID 86707289, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (1 mL) was added to a turbid solution of 2-[2-(4-tert-butylphenyl)ethyl]-N-(2,4-dimethoxybenzyl)-N-[2-fluoro-4-(4-phenylbutoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline-6-sulfonamide obtained (440 mg) in anisole (5 mL) and chloroform (5 mL) while cooling in ice, and the mixture was stirred for 21 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 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=3:1→ethyl acetate only) to afford the title compound as a colorless amorphous substance (240 mg).

Workup

  1. temperaturewhile cooling in ice
  2. temperaturewhile cooling in ice
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationthe desiccant was filtered off
  7. concentrationfollowed by concentration under reduced pressure
  8. customThe resulting residue was purified by NH silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-620be02bb2d84a40892e03b98a4255a5
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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