Pyridine → HCID 86726398, compound

HRID 629786Notes

Reaction equation

HRID 629786 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[C:3]=1[CH:4]=[CH:5][C@H:6]1[O:11][CH2:10][C@@H:9]([CH2:12][OH:13])[N:8]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:7]1.C(C1NC=CN=1)(C1NC=CN=1)=[O:29].[N:40]1[CH:45]=CC=CC=1>>[C:45]([O:13][CH2:12][C@H:9]1[N:8]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:7][C@@H:6](/[CH:5]=[CH:4]/[C:3]2[C:21]([N+:25]([O-:27])=[O:26])=[CH:22][CH:23]=[CH:24][C:2]=2[F:1])[O:11][CH2:10]1)(=[O:29])[NH2:40]

Participants

4

Reactant 3

HCID 1049PyridineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 86726399HCID 86726399, compound

Product 1

HCID 86726398HCID 86726398, compound

Conditions

Temperature
60 °C

Procedure

To a solution of (2R,5R)-tert-butyl 2-[(E)-2-fluoro-6-nitrostyryl)-5-(hydroxymethyl)]morpholine-4-carboxylate (5 g, 13 mmol) from step 2 of Example 99 in pyridine (15 mL) was added carbonyl diimidazole (8.4 g, 52 mmol) and the mixture was heated in sealed tube at 60° C. for 2 h. The reaction mixture was cooled to ambient temperature, then purged with NH3 gas for 5 min and heated in a sealed tube at 60° C. for 16 h. The mixture was cooled to ambient temperature and the solvent was concentrated under reduced pressure. The residue was purified on an 80 g SiO2 column using gradient elution of 0-50% EtOAc in hexanes. Fractions containing product were combined and the solvents were removed under reduced pressure to give the product (5.50 g,) a pale yellow gum.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. custompurged with NH3 gas for 5 min
  3. temperatureheated in a sealed tube at 60° C. for 16 h
  4. temperatureThe mixture was cooled to ambient temperature
  5. concentrationthe solvent was concentrated under reduced pressure
  6. customThe residue was purified on an 80 g SiO2 column
  7. washelution of 0-50% EtOAc in hexanes
  8. additionFractions containing product
  9. customthe solvents were removed under reduced pressure
  10. customto give the product (5.50 g,) a pale yellow gum

Sources & evidence

ORD record
ord-2d36426f42ec4e499a3ddc0aa0342aab
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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