Hydrochloric Acid → HCID 11978592, compound

HRID 1851574Notes

Reaction equation

HRID 1851574 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]([CH3:20])[S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:25]1[S:26][CH:27]=[CH:28][N:29]=1)[N:6]2OCOC.Cl.O1CCCC1.C(O)C>C(OCC)(=O)C>[F:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]([CH3:20])[S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:13])=[O:14])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:25]1[S:26][CH:27]=[CH:28][N:29]=1)[NH:6]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 8028TetrahydrofuranHCID 67109309HCID 67109309, compound

Product 1

HCID 11978592HCID 11978592, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixed solution of N-[4-fluoro-1-(methoxymethoxy)-2-(1,3-thiazol-2-yl)-1H-indol-7-yl]-N-methylthiophene-2-sulfonamide (165 mg), 6N hydrochloric acid (6 mL), tetrahydrofuran (2 mL) and ethanol (4 mL) was stirred at 80° C. for 7 hr. The reaction solution was diluted with ethyl acetate, washed with water, aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:9-3:7), and the obtained crystals were recrystallized from ethyl acetate-hexane to give the title compound (73 mg, yield 49%) as colorless needle crystals. melting point 197-198° C.

Workup

  1. washwashed with water, aqueous sodium hydrogencarbonate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customthe obtained crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-75bb9c6d5ca241d5b746f14bd2f7c162
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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