HCID 19597845, compound → HCID 9935375, compound

HRID 611629Notes

Reaction equation

HRID 611629 reaction equation
[CH:1]([C:4]1[CH:20]=[CH:19][C:7]([CH2:8][NH:9][CH:10]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH3:21][S:22][C:23]1[C:28]([N:29]=[C:30]=[O:31])=[C:27]([S:32][CH3:33])[CH:26]=[C:25]([CH3:34])[N:24]=1>CN(C)C=O.C(OCC)(=O)C>[CH3:21][S:22][C:23]1[C:28]([NH:29][C:30]([N:9]([CH:10]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11]2)[CH2:8][C:7]2[CH:19]=[CH:20][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=2)=[O:31])=[C:27]([S:32][CH3:33])[CH:26]=[C:25]([CH3:34])[N:24]=1

Participants

5

Reactant 2

HCID 19597845HCID 19597845, compoundHCID 19597861HCID 19597861, compound

Product 1

HCID 9935375HCID 9935375, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(4-isopropylbenzylamino)indane (159 mg, 0.6 mmol) and 2,4-bis(methylthio)-6-methylpyridin-3-yl isocyanate (136 mg, 0.6 mmol) in 3 ml dimethylformamide was heated at 80° C. under nitrogen overnight. The reaction mixture was cooled to room temperature, diluted with 50 ml ethyl acetate and washed with 3×50 ml water, then 50 ml brine, dried (sodium sulfate), filtered and concentrated in vacuo. The solid residue (265 mg) was purified by column chromatography on silica gel (150 g), eluting with 7:3 hexane/ethyl acetate to yield the title compound as a white solid (195 mg, 66% yield).

Workup

  1. washwashed with 3×50 ml water
  2. dry with material50 ml brine, dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe solid residue (265 mg) was purified by column chromatography on silica gel (150 g)
  6. washeluting with 7:3 hexane/ethyl acetate

Sources & evidence

ORD record
ord-ddb27b7ddcb9410ca209973f7efd15c3
Source dataset
uspto-grants-1999_12
Patent number
US06001860

Reaction notes

Loading…