Propionyl chloride → HCID 14499841, compound

HRID 2073806Notes

Reaction equation

HRID 2073806 reaction equation
[CH3:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:12]([CH2:16][C:17]#[CH:18])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.[C:24](Cl)(=[O:27])[CH2:25][CH3:26]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:24](=[O:27])[CH2:25][CH3:26])[C:3]=1[CH2:4][NH:5][C:6]1[C:7]2[N:8]([C:12]([CH2:16][C:17]#[CH:18])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 62324Propionyl chlorideHCID 14499840HCID 14499840, compound

Product 1

HCID 14499841HCID 14499841, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 8-(2-methyl-6-aminobenzylamino)-3-(2-propynyl)-2-methlimidazo[1,2-a]pyridine (0.26 g) in chloroform (7.8 ml) was added dropwise propionyl chloride (0.074 ml) at 1°-5° C. and the mixture was stirred for 5 hours at room temperature. The solvent was removed under reduced pressure and the residue was dispersed into a mixture of an aqueous solution of sodium bicarbonate and chloroform. The chloroform layer was separated and washed with water and dried over magnesium sulfate. Following filtration, the solvent was removed under reduced pressure and the residue was triturated with diethyl ether and collected by filitration to give 8-(2-methyl-6-propionylaminobenzylamino)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine (0.25 g).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was dispersed into a mixture of an aqueous solution of sodium bicarbonate and chloroform
  3. customThe chloroform layer was separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltration
  7. customthe solvent was removed under reduced pressure
  8. customthe residue was triturated with diethyl ether
  9. customcollected by filitration

Sources & evidence

ORD record
ord-f0f7aedbbb69457ab03016c13f0ed3f7
Source dataset
uspto-grants-1990_04
Patent number
US04920129

Reaction notes

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