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

HRID 1851781Notes

Reaction equation

HRID 1851781 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, 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.

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-acd4bb77f2f54a87a993eef1245e7383
Source dataset
uspto-grants-2015_02
Patent number
US08957215B2

Reaction notes

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