Water → 5-(5-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

HRID 1698080Notes

Reaction equation

HRID 1698080 reaction equation
F[C:2]1[N:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[CH3:19][NH2:20].O.ClCCl>C(O)C>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:10]2[S:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:20][CH3:19])=[N:7][CH:6]=3)=[N:12][C:11]=2[CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 6344DichloromethaneHCID 575534102-(6-Fluoropyridin-3-yl)-5-methoxy-1,3-benzothiazole

Product 1

HCID 248037275-(5-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To 2-(6-fluoropyridin-3-yl)-5-methoxy-1,3-benzothiazole (59.2 mg, 0.227 mmol) was added methylamine in ethanol (8 M, 2 mL) and the reaction mixture was heated in a microwave oven at 100° C. for 5 min. Water and dichloromethane were added and the layers separated. The aqueous phase was extracted with dichloromethane (3×). The combined organic phases were washed with water, dried (MgSO4), filtered and the solvent removed in vacuo. The crude material was purified by column chromatography (heptane/EtOAc 60:40 to 50:50) to give the title compound (39 mg) as a pale yellow solid. 1H NMR δ ppm 8.68 (d, 1H) 7.98 (dd, 1H) 7.91 (d, 1H) 7.50 (d, 1H) 7.27 (q, 1H) 7.01 (dd, 1H) 6.59 (d, 1H) 3.85 (s, 3H) 2.86 (d, 3H); MS m/z (M+H) 272.

Workup

  1. customthe layers separated
  2. extractionThe aqueous phase was extracted with dichloromethane (3×)
  3. washThe combined organic phases were washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customThe crude material was purified by column chromatography (heptane/EtOAc 60:40 to 50:50)

Sources & evidence

ORD record
ord-6b7d955fc8b44642b5a525abd75766a2
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

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