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

HRID 1698086Notes

Reaction equation

HRID 1698086 reaction equation
CO[C:3]1[CH:20]=[CH:19][C:6]2[N:7]=[C:8]([C:10]3[CH:11]=[N:12][C:13]([N:16]([CH3:18])C)=N[CH:15]=3)[S:9][C:5]=2[CH:4]=1.B(Br)(Br)Br.[Cl-].[Cl-].[Ca+2].[C:28]([O-:31])(O)=O.[Na+].[CH2:33](Cl)Cl>>[CH3:28][O:31][C:20]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]3[CH:15]=[CH:33][C:13]([NH:16][CH3:18])=[N:12][CH:11]=3)=[N:7][C:6]=2[CH:19]=1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 5284359Calcium ChlorideHCID 248040655-(6-methoxy-1,3-benzothiazol-2-yl)-N,N-dimethylpyrimidin-2-amine

Product 1

HCID 248037275-(5-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

Procedure

To a stirred slurry of 5-(6-methoxy-1,3-benzothiazol-2-yl)-N,N-dimethylpyrimidin-2-amine (0.196 mg, 0.68 mmol) in DCM (2 mL) at 0° C. under argon, was added BBr3 (1 M in DCM, 4.1 mL) from a syringe. After 5 min of stirring, the reaction mixture was allowed to reach rt over 6.5 h, while being stirred under a drying tube (CaCl2). Then sat. aq. NaHCO3 was carefully added and the mixture was vigorously stirred at rt on before it was concentrated under vacuum. The residue was dissolved in MeOH, concentrated on and filtered through silica (EtOAc/MeOH 10:1). Purification by HPLC gave the title compound (12 mg) as yellow solid. 1H NMR δ 8.89 (s, 2H) 7.79 (d, 1H) 7.39 (d, 1H) 6.96 (dd, 1H) 3.22 (s, 6H); MS m/z (M+H) 273.

Workup

  1. waitto reach rt over 6.5 h
  2. stirringthe mixture was vigorously stirred at rt on before it
  3. concentrationwas concentrated under vacuum
  4. dissolutionThe residue was dissolved in MeOH
  5. concentrationconcentrated on and
  6. filtrationfiltered through silica (EtOAc/MeOH 10:1)
  7. customPurification by HPLC

Sources & evidence

ORD record
ord-84700304c044456b87fbc8b8e0dcea04
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

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