p-Toluenesulfonic acid → HCID 20813927, compound

HRID 896139Notes

Reaction equation

HRID 896139 reaction equation
[CH3:1][C@@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH2:11])[CH:8]=2)[NH:3]1.[CH2:12]([CH2:16][C:17](=O)[CH3:18])[C:13]([CH3:15])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[CH3:18][C:17]1[N:11]([C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[NH:3][C@H:2]([CH3:1])[CH2:10]3)[C:13]([CH3:15])=[CH:12][CH:16]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80352,5-HexanedioneHCID 45078983HCID 45078983, compound

Product 1

HCID 20813927HCID 20813927, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
68 °C

Procedure

To a stirred solution of (2R)-2,3-dihydro-2-methyl-1H-indol-5-amine (Step 1, 0.896 g, 6.05 mmol) in THF (180 mL) is added acetonylacetone (0.732 mL, 6.05 mmol) and p-toluenesulfonic acid (0.008 g). The reaction mixture is stirred at 68° C. for 6 h and then concentrated under reduced pressure, and the residue is purified by chromatography on a Biotage Flash 40M 90 g silica gel cartridge (10% EtOAc/Hexanes eluent) to give the title compound, MS (ESI+) for C15H18N2 m/z 227 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe residue is purified by chromatography on a Biotage Flash 40M 90 g silica gel cartridge (10% EtOAc/Hexanes eluent)

Sources & evidence

ORD record
ord-b476f232b0eb46879409ea9d8566bdbd
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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