Benzylamine → 4-Benzylamino-6-chloropyridine-3-carboxyamide

HRID 2035482Notes

Reaction equation

HRID 2035482 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][C:3]=1[CH2:9][C:10]([NH2:12])=[O:11].[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)C(C)C)(C)C>C(O)C>[CH2:13]([NH:20][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][C:3]=1[CH2:9][C:10]([NH2:12])=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 1317309314,6-Dichloropyridine-3-carboxyamide

Product 1

HCID 1317309304-Benzylamino-6-chloropyridine-3-carboxyamideYield 88.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.00 g of 4,6-dichloropyridine-3-carboxyamide synthesized according to the method described in US 2006/0217417 was dissolved in 50 mL of ethanol, to which 3.37 g of benzylamine and 4.40 g of N,N-diisopropylethylamine were added, and heated at reflux for 12 hours. After cooling, the solvent was evaporated, and 100 mL of water was added to the residue. After cooling with ice, the deposited crystals were filtered, washed with water and hexane, and air-dried. It was further dried under reduced pressure (100° C., 2 hours) to obtain the title compound (5.96 g, 87%) as light yellow needle crystals.

Workup

  1. additionwere added
  2. temperatureheated
  3. temperatureat reflux for 12 hours
  4. temperatureAfter cooling
  5. customthe solvent was evaporated
  6. addition100 mL of water was added to the residue
  7. temperatureAfter cooling with ice
  8. filtrationthe deposited crystals were filtered
  9. washwashed with water and hexane
  10. customair-dried
  11. customIt was further dried under reduced pressure (100° C., 2 hours)

Sources & evidence

ORD record
ord-3bd9051c88f447a89e495a4a8183fa6f
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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