HCID 22612049, compound → HCID 22612219, compound

HRID 844057Notes

Reaction equation

HRID 844057 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:13][C:14]2[C:15]([O:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[N:16][CH:17]=[CH:18][CH:19]=2)=[O:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:27][Li]>O1CCCC1>[OH:3][C:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]([NH:13][C:14]2[C:15]([O:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[N:16][CH:17]=[CH:18][CH:19]=2)=[O:12])=[CH:8][CH:9]=1)([CH3:27])[CH3:2]

Participants

4

Reactant 2

HCID 22612049HCID 22612049, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 22612219HCID 22612219, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-(4-Acetyl-phenyl)-N-[2-(pyridin-3-yloxy)-pyridin-3-yl]-acetamide (0.130 grams, 0.374 mmole) in tetrahydrofuran (10 ml) at −78° C. 1.0 M methyl lithium in tetrahydrofuran (1.123 ml, 1.123 mmole) was added and stirred at −78° C. for 30 minutes, allowed to warm to room temperature for 30 minutes and cooled to −78° C. The mixture was quenched with water and extracted with ethyl acetate. The combined organics were washed with water and brine, dried over MgSO4, filtered and concentrated to a product which was purified by chromatography on silica eluting with 3% methanol/methylene chloride. Recrystalization from ethyl acetate/hexane gave a solid (0.045 g). M.P. 122-124° C.; Anal. calcd. for C21H21N3O3: C, 69.41; H, 5.82; N, 11.50. Found: C, 69.02; H, 6.12; N, 11.30.

Workup

  1. customat −78° C
  2. temperatureto warm to room temperature for 30 minutes
  3. temperaturecooled to −78° C
  4. customThe mixture was quenched with water
  5. extractionextracted with ethyl acetate
  6. washThe combined organics were washed with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to a product which
  10. customwas purified by chromatography on silica eluting with 3% methanol/methylene chloride
  11. customRecrystalization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-c095559857ea4520989bac4718d2a447
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

Loading…