Pyridine → HCID 11724681, compound

HRID 2226653Notes

Reaction equation

HRID 2226653 reaction equation
[NH2:1][C:2]([C:4]1[O:8][N:7]=[C:6]([C:9]2[CH:24]=[C:23]([CH3:25])[C:12]([O:13][CH2:14][CH2:15][CH2:16][C:17]3[O:21][N:20]=[C:19]([CH3:22])[CH:18]=3)=[C:11]([CH3:26])[CH:10]=2)[N:5]=1)=O.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCCC1.O>[C:2]([C:4]1[O:8][N:7]=[C:6]([C:9]2[CH:10]=[C:11]([CH3:26])[C:12]([O:13][CH2:14][CH2:15][CH2:16][C:17]3[O:21][N:20]=[C:19]([CH3:22])[CH:18]=3)=[C:23]([CH3:25])[CH:24]=2)[N:5]=1)#[N:1]

Participants

6

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 10021155HCID 10021155, compound

Product 1

HCID 11724681HCID 11724681, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a chilled (0° C.) suspension of the product of Example 38 (1.60 g, 4.50 mmol) and dry pyridine (11.2 mL) in dry tetrahydrofuran (27 mL) was added trifluoroacetic anhydride (1.90 mL, 13.5 mmol). The mixture was stirred at 0° C. for 4 hours and at room temperature for 18 hours, diluted with water (100 mL), and extracted with ethyl acetate (2×25 mL). The combined organic phases were washed with 1N HCl (3×), brine, dried (MgSO4), and concentrated in vacuo. The red solid obtained (1.67 g) was chromatographed (Silica Gel 60, 20% ethyl acetate in hexanes) to give 1.38 g (90.8%) of pure title compound as a white solid, mp 93°-4° C. (ethyl acetate and hexanes).

Workup

  1. temperatureTo a chilled
  2. extractionextracted with ethyl acetate (2×25 mL)
  3. washThe combined organic phases were washed with 1N HCl (3×), brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe red solid obtained (1.67 g)
  7. customwas chromatographed (Silica Gel 60, 20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-70ffe845ce7147fea64d072df49be5b4
Source dataset
uspto-grants-1994_09
Patent number
US05349068

Reaction notes

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