6-(Methoxymethoxy)indan-5-amine → N-[6-(methoxymethoxy)-2,3-dihydro-1H-inden-5-yl]-4-methyl-1,3-thiazole-2-sulfonamide

HRID 1879405Notes

Reaction equation

HRID 1879405 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH2:11]2)=[CH:7][C:6]=1[NH2:14].[CH3:15][C:16]1[N:17]=[C:18]([S:21](Cl)(=[O:23])=[O:22])[S:19][CH:20]=1.COC(C)(C)C>N1C=CC=CC=1>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH2:11]2)=[CH:7][C:6]=1[NH:14][S:21]([C:18]1[S:19][CH:20]=[C:16]([CH3:15])[N:17]=1)(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 583985166-(Methoxymethoxy)indan-5-amineHCID 866565784-Methyl-1,3-thiazole-2-sulfonylchloride tert-butyl methyl ether

Product 1

HCID 58398543N-[6-(methoxymethoxy)-2,3-dihydro-1H-inden-5-yl]-4-methyl-1,3-thiazole-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3.30 g of 6-(methoxymethoxy)indan-5-amine was dissolved in 33.0 mL of pyridine and 157 mL of a 0.54 M 4-methyl-1,3-thiazole-2-sulfonylchloride/tert-butyl methyl ether solution was added thereto, followed by stirring overnight at room temperature. The reaction liquid was concentrated under reduced pressure, to the residue were added water and ethyl acetate, and the insoluble materials were removed by filtration. After the filtrate was extracted with ethyl acetate, the organic layer was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=73:27 to 60:40) to obtain 4.79 g of N-[6-(methoxymethoxy)-2,3-dihydro-1H-inden-5-yl]-4-methyl-1,3-thiazole-2-sulfonamide.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure, to the residue
  3. additionwere added water and ethyl acetate
  4. customthe insoluble materials were removed by filtration
  5. extractionAfter the filtrate was extracted with ethyl acetate
  6. washthe organic layer was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=73:27 to 60:40)

Sources & evidence

ORD record
ord-5ff95aa92d3e4077ad2bbac258a73c6c
Source dataset
uspto-grants-2012_11
Patent number
US08314240B2

Reaction notes

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