Sodium Bicarbonate → 5-(1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

Reaction equation

C(O[C:4]1[N: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][CH:5]=1)C.[CH3:21][N:22](C)C1N=CC(C2SC3C=C(O)C=CC=3N=2)=CN=1.C([O-])(O)=O.[Na+]>>[S:11]1[C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=[C:10]1[C:7]1[CH:6]=[CH:5][C:4]([NH:22][CH3:21])=[N:9][CH:8]=1

Participants

Reactant 3

HCID 516892Sodium Bicarbonate

HCID 248038932-(6-Ethoxypyridin-3-yl)-6-methoxy-1,3-benzothiazole

HCID 248040662-[2-(Dimethylamino)pyrimidin-5-yl]-1,3-benzothiazol-6-ol

Product 1

HCID 248042395-(1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

Procedure

2-(6-Ethoxypyridin-3-yl)-6-methoxy-1,3-benzothiazole (23 mg, 80 μmol) was reacted according to the procedure used for the preparation of 2-[2-(dimethylamino)pyrimidin-5-yl]-1,3-benzothiazol-6-ol, with the following exceptions: The reaction mixture was allowed to reach rt on. sat. aq. NaHCO3 was added and the mixture was extracted with EtOAc. The organic phase was dried and concentrated under reduced pressure. Preparative HPLC of the residue gave the title compound (4 mg). 1H NMR (CHLOROFORM-d: CD3OD) δ 8.69 (d, 1 H) 8.20 (dd, 1 H) 7.79 (d, 1 H) 7.29 (d, 1 H) 6.99 (dd, 1 H) 6.86 (d, 1H) 4.39 (q, 2 H) 1.41 (t, 3 H); MS m/z (M+H) 273.