Dimethylamine → HCID 58442389, compound

HRID 1843814Notes

Reaction equation

HRID 1843814 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][N:24]=1)[C:5]([NH:7][C:8]1[S:9][CH:10]=[C:11]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=2[CH3:21])[N:12]=1)=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:31][NH:32][CH3:33].C1COCC1>CN(C=O)C.O>[CH3:31][N:32]([CH3:33])[C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][N:24]=1)[C:5]([NH:7][C:8]1[S:9][CH:10]=[C:11]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=2[CH3:21])[N:12]=1)=[O:6]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 58442440HCID 58442440, compound

Product 1

HCID 58442389HCID 58442389, compoundYield 3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chloro-N-(4-mesitylthiazol-2-yl)isonicotinamide (200 mg, 0.60 mmol, 1.0 equiv), caesium carbonate (2.73 g, 0.6 mmol, 15 equiv) and 2.0 M dimethylamine in THF (3.4 mL, 6.7 mmol, 12 equiv) in DMF (6.0 mL) was heated at reflux for 16 h. The mixture was poured into icy H2O (10.0 mL) and extracted with EtOAc. The organic layer was collected, dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (15% EtOAc in hexanes as eluant) to provide 2-(dimethylamino)-N-(4-mesityl-thiazol-2-yl)isonicotinamide (5.5 mg, 0.10 mmol) as yellow solids in 3.0% yield: 1H NMR (CDCl3, 500 MHz) δ 8.32 (d, J=5.1 Hz, 1 H), 7.02 (s, 1 H), 6.92 (s, 2 H), 6.85 (d, J=5.1 Hz, 1 H), 6.80 (s, 1 H), 3.16 (s, 6 H), 2.31 (s, 3 H), 2.09 (s, 6 H); ESI-MS: m/z 367.1 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. extractionextracted with EtOAc
  4. customThe organic layer was collected
  5. dry with materialdried over MgSO4(s)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (15% EtOAc in hexanes as eluant)

Sources & evidence

ORD record
ord-4370a25f8bcf411b92c07bc5b71373fa
Source dataset
uspto-grants-2015_02
Patent number
US08946268B2

Reaction notes

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