N-Methylbenzeneethanamine → HCID 53250185, compound

HRID 1043507Notes

Reaction equation

HRID 1043507 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CCN(C(C)C)C(C)C.Br[C:21]1[N:26]=[C:25](/[CH:27]=[C:28]2/[C:29](=[O:34])[NH:30][C:31](=[O:33])[S:32]/2)[CH:24]=[CH:23][CH:22]=1>CS(C)=O>[CH3:1][N:2]([CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:21]1[N:26]=[C:25](/[CH:27]=[C:28]2/[C:29](=[O:34])[NH:30][C:31](=[O:33])[S:32]/2)[CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 11503N-MethylbenzeneethanamineHCID 81531DiisopropylethylamineHCID 58312892HCID 58312892, compound

Product 1

HCID 53250185HCID 53250185, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

An 8 mL round-bottomed vial was charged with N-methyl-2-phenylethanamine (43 mg, 0.318 mmol, 1 equiv.) and DMSO (1 mL, 0.3 M), DiPEA (105 μL, 0.636 mmol, 2 equiv.), (Z)-5-((6-bromopyridin-2-yl)methylene)thiazolidine-2,4-dione (91 mg, 0.318 mmol, 1 equiv.), and the vial was purged with argon. The mixture was shaken for 48 h at 110° C. The reaction mixture was then partitioned between CH2Cl2 (10 mL) and sat. NaCl (20 mL). The aqueous layer was back extracted with CH2Cl2 (2×15 mL) and the combined organic layer was dried over xxx and concentrated under reduced pressure to provide an orange residue. The orange residue was triturated with ether (3×15 mL) to provide (Z)-5-((6-(methyl(phenethyl)amino)pyridin-2-yl)methylene)thiazolidine-2,4-dione as an orange film (2.6 mg, 175 mg theoretical, 5%). LC-MS m/z: 340 (M+1).

Workup

  1. customthe vial was purged with argon
  2. customThe reaction mixture was then partitioned between CH2Cl2 (10 mL) and sat. NaCl (20 mL)
  3. extractionThe aqueous layer was back extracted with CH2Cl2 (2×15 mL)
  4. dry with materialthe combined organic layer was dried over xxx
  5. concentrationconcentrated under reduced pressure
  6. customto provide an orange residue
  7. customThe orange residue was triturated with ether (3×15 mL)

Sources & evidence

ORD record
ord-799aed1de928471daa57d5f281d815ad
Source dataset
uspto-grants-2013_10
Patent number
US08563539B2

Reaction notes

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