Triethylamine → Sch 28080

HRID 544447Notes

Reaction equation

HRID 544447 reaction equation
Cl[CH:2]([C:6](=O)[CH3:7])[CH2:3][C:4]#[N:5].[NH2:9][C:10]1[C:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=[CH:12][N:11]=1.C(N(CC)CC)C>C(O)C>[CH2:17]([O:16][C:15]1[C:10]2[N:11]([C:2]([CH2:3][C:4]#[N:5])=[C:6]([CH3:7])[N:9]=2)[CH:12]=[CH:13][CH:14]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 903342-Amino-3-benzyloxypyridineHCID 139002363-Chloro-4-oxopentanenitrile

Product 1

HCID 108137Sch 28080

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.86 g. of 3-chloro-4-oxopentanonitrile, 0.92 g. of 2-amino-3-phenylmethoxypyridine and 0.5 ml. of triethylamine in 15 ml. of ethanol was stirred for 16 hours, then concentrated to remove the triethylamine and ethanol. The residue was dissolved in methylene chlorideand washed with water. The methylene chloride was concentrated and the residual oil was dissolved in 20 ml. of boiling acetonitrile, filtered, cooled, and treated with hydrogen chloride/methanol with cooling to give 0.22 g. of the desired product (m.p. 163°-166° C.).

Workup

  1. concentrationconcentrated
  2. customto remove the triethylamine and ethanol
  3. dissolutionThe residue was dissolved in methylene
  4. washchlorideand washed with water
  5. concentrationThe methylene chloride was concentrated
  6. dissolutionthe residual oil was dissolved in 20 ml
  7. filtrationof boiling acetonitrile, filtered
  8. temperaturecooled
  9. additiontreated with hydrogen chloride/methanol
  10. temperaturewith cooling
  11. customto give 0.22 g

Sources & evidence

ORD record
ord-cda23162da864db180393d4694b21bf1
Source dataset
uspto-grants-1984_05
Patent number
US04450164

Reaction notes

Loading…