Dichloromethane → HCID 22715001, compound

HRID 352017Notes

Reaction equation

HRID 352017 reaction equation
ClCCl.[Cl:4][C:5]1[C:10]([NH2:11])=[C:9]([NH:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH:8]=[C:7]([CH3:17])[N:6]=1.[CH2:18]([O:20][CH2:21][C:22](Cl)=[O:23])[CH3:19]>C(N(CC)CC)C>[Cl:4][C:5]1[C:10]([NH:11][C:22](=[O:23])[CH2:21][O:20][CH2:18][CH3:19])=[C:9]([NH:12][CH2:13][CH:14]([CH3:15])[CH3:16])[CH:8]=[C:7]([CH3:17])[N:6]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 84189Ethoxyacetyl chlorideHCID 227150032-Chloro-N4-(2-methylpropyl)-6-methylpyridin-3,4-diamine

Product 1

HCID 22715001HCID 22715001, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

Anhydrous dichloromethane (300 ml), 2-chloro-N4-(2-methylpropyl)-6-methyl pyridin-3,4-diamine (4.14 g) from Part B and triethylamine (2.93 ml) were combined and cooled to 0° C. To the resulting mixture was added dropwise ethoxyacetyl chloride (2.49 g). After 1 hour the resulting reaction mixture was allowed to warm to room temperature. After 2 hours, the reaction, monitored by HPLC, was complete, and the solvent was removed under reduced pressure. The resulting yellow oil was dissolved in ethyl acetate, and the resulting solution was washed with water. The organic layer was dried with magnesium sulfate and concentrated to a yellow oil under reduced pressure. The yellow oil was put through a column of silica gel using 20/80 ethyl acetate/hexane. NMR analysis of the oil obtained after removal of the solvent under reduce pressure indicated desired product (3.64 g) of good purity for use in the next step.

Workup

  1. customAfter 1 hour the resulting reaction mixture
  2. temperatureto warm to room temperature
  3. customthe reaction
  4. customthe solvent was removed under reduced pressure
  5. dissolutionThe resulting yellow oil was dissolved in ethyl acetate
  6. washthe resulting solution was washed with water
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. concentrationconcentrated to a yellow oil under reduced pressure
  9. customNMR analysis of the oil obtained
  10. customafter removal of the solvent

Sources & evidence

ORD record
ord-0e650aef6c2e48deb2f8a86d8d1f0849
Source dataset
uspto-grants-2004_06
Patent number
US06743920B2

Reaction notes

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