Hydrochloric Acid → HCID 86703290, compound

HRID 2409971Notes

Reaction equation

HRID 2409971 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=3)[C:12]([CH2:21][C:22]3[N:27]=[C:26]([C:28]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])=[O:29])[CH:25]=[CH:24][CH:23]=3)=[C:11]2[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)(=O)=O)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>O1CCCC1.CO>[CH3:34][S:31]([NH:30][C:28]([C:26]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:21][C:12]2[C:13]3[C:18](=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[NH:10][C:11]=2[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:27]=1)=[O:29])(=[O:32])=[O:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10796Cesium carbonate2×HCID 86703274HCID 86703274, compound

Product 1

HCID 86703290HCID 86703290, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 6-(1-benzenesulfonyl-6-methoxy-2-phenyl-1H-indol-3-ylmethyl)-N-methanesulfonylpyridine-2-carboxamide (632 mg) in tetrahydrofuran/methanol (7.4 mL/3.7 mL) was added cesium carbonate (1.43 g), and this mixture was stirred at 50° C. for 29 hours. Cesium carbonate (1.43 g) was added thereto, and further stirred for additional 45.5 hours. The reaction mixture was left to be cooled. To the reaction mixture was added 1 mol/L hydrochloric acid (20 mL), followed by extraction with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: methanol-dichloromethane) to obtain the title compound (375 mg).

Workup

  1. stirringfurther stirred for additional 45.5 hours
  2. waitThe reaction mixture was left
  3. temperatureto be cooled
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluting solvent: methanol-dichloromethane)

Sources & evidence

ORD record
ord-738e9ada66d5407b96ced28978b0c6b4
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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