Pyridine → HCID 86675960, compound

HRID 2039760Notes

Reaction equation

HRID 2039760 reaction equation
N1C=CC=CC=1.[Cl:7][C:8]1[C:13]([NH2:14])=[CH:12][CH:11]=[C:10]([Cl:15])[N:9]=1.[CH3:16][O:17][C:18]1[C:26]([CH3:27])=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][C:19]=1[CH3:28].S(=O)(=O)(O)[O-].[Na+]>ClCCl>[Cl:7][C:8]1[C:13]([NH:14][C:22](=[O:23])[C:21]2[CH:25]=[C:26]([CH3:27])[C:18]([O:17][CH3:16])=[C:19]([CH3:28])[CH:20]=2)=[CH:12][CH:11]=[C:10]([Cl:15])[N:9]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 1128462,6-Dichloro-3-pyridylamineHCID 516919Sodium BisulfateHCID 214353833,5-Dimethyl-4-methoxybenzoyl chloride

Product 1

HCID 86675960HCID 86675960, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

With ice cooling, a solution of 2.7 ml of absolute pyridine in 5 ml of dry dichloromethane was initially added dropwise to a solution of 5.00 g of 2,6-dichloropyridin-3-ylamine in 50 ml of dry dichloromethane. 6.70 g of 4-methoxy-3,5-dimethylbenzoyl chloride, dissolved in 15 ml of dry dichloromethane, were then added, and the reaction was stirred at 0° C. for 1 h and then at room temperature for 16 h. 10% strength aqueous sodium bisulfate solution was then added, and the mixture was stirred for 15 minutes. The phases were then separated, and the aqueous phase was extracted twice with dichloromethane. The collected organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. This gave 10.00 g (100%) of the product, which was used for the next step without any further purification.

Workup

  1. additionwere then added
  2. waitat room temperature for 16 h
  3. stirringthe mixture was stirred for 15 minutes
  4. customThe phases were then separated
  5. extractionthe aqueous phase was extracted twice with dichloromethane
  6. dry with materialThe collected organic phases were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThis gave 10.00 g (100%) of the product, which was used for the next step without any further purification

Sources & evidence

ORD record
ord-322da7ead7764df2b7c10c82cd58ac08
Source dataset
uspto-grants-2013_11
Patent number
US08580816B2

Reaction notes

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