2-[6-(Ethylamino)pyridin-3-yl]-1,3-benzothiazol-6-ol → 5-(5-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine
Reaction equation
C([N:3]([CH3:21])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]3[CH:18]=[C:17](OC)[CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:6][N:5]=1)C.C(NC1N=CC(C2SC3C=[C:38]([OH:40])C=CC=3N=2)=CC=1)C>>[CH3:38][O:40][C:16]1[CH:17]=[CH:18][C:12]2[S:11][C:10]([C:7]3[CH:8]=[CH:9][C:4]([NH:3][CH3:21])=[N:5][CH:6]=3)=[N:14][C:13]=2[CH:15]=1Participants
3
Procedure
N-Ethyl-5-(6-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine (55.4 mg, 0.185 mmol) was subjected to the procedure described for 2-[6-(ethylamino)pyridin-3-yl]-1,3-benzothiazol-6-ol. Recrystallization from methanol gave 23.7 mg of the title compound as a pale yellow solid. 1H NMR δ ppm 9.75 (s, 1H) 8.67 (d, 1H) 8.03 (dd, 1H) 7.75 (d, 1H) 7.35 (d, 1H) 6.93 (dd, 1H) 6.75 (d, 1H) 3.63 (q, 2H) 3.07 (s, 3H) 1.11 (t, 3H); MS m/z (M+H) 286.
Workup
- customRecrystallization from methanol