Anisole → HCID 58452450, compound

HRID 70692Notes

Reaction equation

HRID 70692 reaction equation
C1(OC)C=CC=CC=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13](/[C:16](/[C:35]2[NH:40][C:39](=[O:41])[C:38]([C:42]3[CH:43]=[N:44][NH:45][CH:46]=3)=[CH:37][CH:36]=2)=[CH:17]\[C@H:18]2[CH2:22][CH2:21][C:20](=[O:23])[N:19]2CC2C=CC(OC)=CC=2OC)=[CH:12][CH:11]=1>FC(F)(F)C(O)=O>[Cl:9][C:10]1[CH:11]=[CH:12][C:13](/[C:16](/[C:35]2[NH:40][C:39](=[O:41])[C:38]([C:42]3[CH:46]=[N:45][NH:44][CH:43]=3)=[CH:37][CH:36]=2)=[CH:17]\[C@H:18]2[CH2:22][CH2:21][C:20](=[O:23])[NH:19]2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 67398115HCID 67398115, compound

Product 1

HCID 58452450HCID 58452450, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
70 °C

Procedure

Anisole (0.5 mL) was added to a solution of 6-{(E)-1-(4-chlorophenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-3-(1H-pyrazol-4-yl)pyridin-2(1H)-one (100 mg) in trifluoroacetic acid (1 mL), and the mixture was stirred at 70° C. for five hours. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=1:0→9:1) and recrystallized from ethyl acetate-hexane to give the title compound as a pale yellow powder (51.2 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (chloroform:methanol=1:0→9:1)
  3. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-4ffdc54072a6461893617920ba84ebff
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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