Triethylamine → HCID 19815934, compound

HRID 2247873Notes

Reaction equation

HRID 2247873 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:12]=[C:11]([CH3:21])[C:10]=2C(O)=O)[CH:6]=[CH:7][CH:8]=1)#[N:2].C1(P([N:39]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>C(O)(C)(C)C>[NH2:39][C:10]1[C:11]([CH3:21])=[N:12][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:14][C:9]=1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 19815960HCID 19815960, compound

Product 1

HCID 19815934HCID 19815934, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(3-cyanophenyl)-2-methyl-6-phenyl-3-pyridinecarboxylic acid (3.7 g), diphenylphosphoryl azide (3.24 g), triethylamine (1.19 g) and t-butanol (35 ml) was refluxed for 5 hours. After the organic solvent was evaporated, chloroform (40 ml) and a saturated aqueous solution of sodium bicarbonate (40 ml) were added to the residue. The separated organic layer was washed with water and brine, dried and concentrated in vacuo. The residue containing 3-(t-butoxycarbonylamino)-4-(3-cyanophenyl)-2-methyl-6-phenylpyridine was dissolved with ethanol (35 ml). After conc. hydrochloric acid (2 ml) was added to the solution at 0° C., the mixture was stirred at 0° C. for 1.5 hours and further at 80° C. for 7.5 hours. The mixture was concentrated, dissolved with chloroform (40 ml) and water (40 ml) and adjusted to pH 9 with 5N sodium hydroxide. The organic layer was separated, washed with brine, dried and concentrated in vacuo. The residue was purified by column chromatography on silica gel (70 g) eluting with a mixture of chloroform and methanol (100:1 V/V). The fractions containing the desired compound were combined and concentrated in vacuo. The residue was triturated with diethyl ether to give 3-amino-4-(3-cyanophenyl)-2-methyl-6-phenylpyridine (1.30 g).

Workup

  1. temperaturewas refluxed for 5 hours
  2. customAfter the organic solvent was evaporated
  3. additionchloroform (40 ml) and a saturated aqueous solution of sodium bicarbonate (40 ml) were added to the residue
  4. washThe separated organic layer was washed with water and brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. additionThe residue containing 3-(t-butoxycarbonylamino)-4-(3-cyanophenyl)-2-methyl-6-phenylpyridine
  8. dissolutionwas dissolved with ethanol (35 ml)
  9. additionAfter conc. hydrochloric acid (2 ml) was added to the solution at 0° C.
  10. concentrationThe mixture was concentrated
  11. dissolutiondissolved with chloroform (40 ml) and water (40 ml)
  12. customThe organic layer was separated
  13. washwashed with brine
  14. customdried
  15. concentrationconcentrated in vacuo
  16. customThe residue was purified by column chromatography on silica gel (70 g)
  17. washeluting with a mixture of chloroform and methanol (100:1 V/V)
  18. additionThe fractions containing the desired compound
  19. concentrationconcentrated in vacuo
  20. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-6959c21e7278411caea0f7fe235b27ec
Source dataset
uspto-grants-1991_08
Patent number
US05037824

Reaction notes

Loading…