Pyridine → HCID 23056777, compound

HRID 1054964Notes

Reaction equation

HRID 1054964 reaction equation
CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[NH2:14][N:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]1=[NH2+:22].[Cl:23][CH2:24][C:25](Cl)=O.N1C=CC=CC=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[Cl:21][C:19]1[CH:18]=[CH:17][C:16]2[N:15]([N:14]=[C:25]([CH2:24][Cl:23])[N:22]=2)[CH:20]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 178425984HCID 178425984, compound

Product 1

HCID 23056777HCID 23056777, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-amino-5-chloropyridin-2(1H)-iminium 2,4,6-trimethylbenzenesulfonate (500 mg, 1.45 mmol, Eq: 1.00), 2-chloroacetyl chloride (172 mg, 122 μl, 1.53 mmol, Eq: 1.05) and pyridine (242 mg, 247 μl, 3.05 mmol, Eq: 2.1) in DMF (5.00 ml) was stirred at 90° C. for 2 h. The mixture was poured on 20 ml half saturated aq. NaHCO3 and extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and concentrated to an oil. Purification by column chromatography (SiO2, 0 to 80% EtOAc in n-heptane) gave the desired product (68 mg, 23%) as a white solid. MS m/z=202.1 (M+H+)

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to an oil
  5. customPurification by column chromatography (SiO2, 0 to 80% EtOAc in n-heptane)

Sources & evidence

ORD record
ord-e7e81996a18e43efa52084be1db7e09c
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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