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

HRID 1698100Notes

Reaction equation

HRID 1698100 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

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 248038932-(6-Ethoxypyridin-3-yl)-6-methoxy-1,3-benzothiazoleHCID 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, 1H) 8.20 (dd, 1H) 7.79 (d, 1H) 7.29 (d, 1H) 6.99 (dd, 1H) 6.86 (d, 1H) 4.39 (q, 2H) 1.41 (t, 3H); MS m/z (M+H) 273.

Workup

  1. customto reach rt
  2. extractionthe mixture was extracted with EtOAc
  3. customThe organic phase was dried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4cd9ab477c4d419f978179f92d651064
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

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