2-Chloro-6-methoxy-3-nitropyridine → HCID 86681010, compound

HRID 1847976Notes

Reaction equation

HRID 1847976 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:11][CH3:12])[N:3]=1.[CH3:13][S:14][C:15]1[S:16][C:17]2[CH:23]=[C:22]([CH2:24][NH2:25])[CH:21]=[CH:20][C:18]=2[N:19]=1>CN(C=O)C.CCOC(C)=O>[CH3:12][O:11][C:4]1[N:3]=[C:2]([NH:25][CH2:24][C:22]2[CH:21]=[CH:20][C:18]3[N:19]=[C:15]([S:14][CH3:13])[S:16][C:17]=3[CH:23]=2)[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 27950292-Chloro-6-methoxy-3-nitropyridineHCID 86681009HCID 86681009, compound

Product 1

HCID 86681010HCID 86681010, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-6-methoxy-3-nitropyridine (430 mg, 2.3 mmol) in DMF (6 mL) was added (2-(methylthio)benzo[d]thiazol-6-yl)methanamine (437 mg, 2.1 mmol) from Step 4 of this Example slowly at 0° C. The reaction mixture was stirred at rt overnight. The resulting reaction mixture was diluted with 60 mL of EtOAc and washed with saturated aq NaHCO3 and brine. The organic layer was dried over MgSO4, and concentrated under reduced pressure. The crude product was purified on a silica gel column using CH2Cl2 as eluent to give 6-methoxy-N-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)-3-nitropyridin-2-amine as a yellow solid (431 mg, 57%). LCMS (ESI) m/z 363 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. washwashed with saturated aq NaHCO3 and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified on a silica gel column

Sources & evidence

ORD record
ord-95d56f8237534c4eb1afb6b030e83761
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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