Methyl iodide → N-methyl-N-(4-methoxyphenyl)-4-pyridin-4-yl-1,3-thiazol-2-amine

HRID 1592968

Reaktionsgleichung

Reaktionsgleichung von HRID 1592968
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[N:14]=2)=[CH:5][CH:4]=1.[H-].[Na+].[CH3:23]I>CN(C=O)C>[CH3:23][N:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:10]1[S:11][CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[N:14]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 793675N-(4-methoxyphenyl)-4-pyridin-4-yl-1,3-thiazol-2-amine

Produkt 1

HCID 11220215N-methyl-N-(4-methoxyphenyl)-4-pyridin-4-yl-1,3-thiazol-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N-(4-methoxyphenyl)-4-pyridin-4-yl-1,3-thiazol-2-amine (7-2, 0.1 g, 0.36 mmol) was dissolved in 1 mL DMF. NaH (0.02 g, 0.7 mmol) was added and the suspension was allowed to stir for 2 min. MeI (0.02 mL, 0.36 mmol) was added and the reaction was allowed to stir for 1 h. The reaction was quenched with water and the products extracted with EtOAc. The organic layer was concentrated to 0.5 mL then purified on a Gilson automated system affixed with a YMC Combiflash 50×20 mm column eluted at 30 mL/min with 5-65% CH3CN in H2O (both containing 0.1% TFA) over 10.5 min to yield N-methyl-N-(4-methoxyphenyl)-4-pyridin-4-yl-1,3-thiazol-2-amine (8-1): 1H NMR (500 MHz, CDCl3) δ 8.60 (d, J=1 Hz, 2H), 7.72 (d, J=1 Hz, 2H), 7.3 (d, J=3 Hz, 2H), 6.97 (d, J=3 Hz, 2H), 6.88 (s, 1H), 3.85 (s, 3H), 3.57 (s, 3H): MS 298.3 found 298.2 (M+H+).

Aufarbeitung

  1. stirringto stir for 1 h
  2. customThe reaction was quenched with water
  3. extractionthe products extracted with EtOAc
  4. concentrationThe organic layer was concentrated to 0.5 mL
  5. customthen purified on a Gilson automated system
  6. washeluted at 30 mL/min with 5-65% CH3CN in H2O (both containing 0.1% TFA) over 10.5 min

Quellen und Nachweise

ORD-Eintrag
ord-e13aacaabfbc4d80888fd16de488b0af
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07294640B2

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