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

HRID 1851761Notes

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

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, 1 H) 7.98 (dd, 1 H) 7.91 (d, 1 H) 7.50 (d, 1 H) 7.27 (q, 1 H) 7.01 (dd, 1 H) 6.59 (d, 1 H) 3.85 (s, 3 H) 2.86 (d, 3 H); MS m/z (M+H) 272.

Workup

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

Sources & evidence

ORD record: ord-7a23ea1a0ad04764bb206eb8ab734a79
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957215B2

Reaction notes

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