Sodium Carbonate → 3-Nitro-6-chloro-N-(thiazolo[4,5-c]pyridin-2-ylmethyl)pyridin-2-amine

HRID 1890595Notes

Reaction equation

HRID 1890595 reaction equation
[N+:1]([C:4]1[C:5](Cl)=[N:6][C:7]([Cl:10])=[CH:8][CH:9]=1)([O-:3])=[O:2].C([O-])([O-])=O.[Na+].[Na+].[S:18]1[C:26]2[CH:25]=[CH:24][N:23]=[CH:22][C:21]=2[N:20]=[C:19]1[CH2:27][NH2:28]>C(O)(C)C>[N+:1]([C:4]1[C:5]([NH:28][CH2:27][C:19]2[S:18][C:26]3[CH:25]=[CH:24][N:23]=[CH:22][C:21]=3[N:20]=2)=[N:6][C:7]([Cl:10])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 852392,6-Dichloro-3-nitropyridineHCID 65441030Thiazolo[4,5-c]pyridine-2-methanamine

Product 1

HCID 866714403-Nitro-6-chloro-N-(thiazolo[4,5-c]pyridin-2-ylmethyl)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 3-nitro-2,6-dichloropyridine (106 mg, 0.55 mmol) in isopropanol (3 mL) was sequentially added Na2CO3 (116 mg, 1.1 mmol) and intermediate R (100 mg, 0.61 mmol). The reaction mixture was stirred at room temperature overnight, and then concentrated. The residue was extracted with EtOAc. The organic layer was separated, concentrated, and purified by chromatography on silica gel to afford the title compound. MS (m/z): 322 (M)+.

Workup

  1. concentrationconcentrated
  2. extractionThe residue was extracted with EtOAc
  3. customThe organic layer was separated
  4. concentrationconcentrated
  5. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-a9877dc3c3c24326a5514c0dddc70b26
Source dataset
uspto-grants-2013_08
Patent number
US08507487B2

Reaction notes

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