HCID 67236264, compound → HCID 53241502, compound

HRID 1023627Notes

Reaction equation

HRID 1023627 reaction equation
[CH2:1]([C@:3]1([CH3:28])[C:7](=[O:8])[N:6]([C:9]2[CH:10]=[CH:11][C:12]([O:15][C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([C:24]([CH3:26])=[CH2:25])[CH:17]=3)=[N:13][CH:14]=2)[C:5](=[O:27])[NH:4]1)[CH3:2]>CO>[CH2:1]([C@:3]1([CH3:28])[C:7](=[O:8])[N:6]([C:9]2[CH:10]=[CH:11][C:12]([O:15][C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([CH:24]([CH3:25])[CH3:26])[CH:17]=3)=[N:13][CH:14]=2)[C:5](=[O:27])[NH:4]1)[CH3:2]

Participants

3

Reactant 1

HCID 67236264HCID 67236264, compound2×

Product 1

HCID 53241502HCID 53241502, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-({5-[(4R)-4-ethyl-4-methyl-2,5-dioxo-1-imidazolidinyl]-2-pyridinyl}oxy)-2-(1-methylethenyl)benzonitrile (Intermediate 207, 98 mg) in MeOH (10 mL) Pd 10% w/w on activate carbon (10 mg) was added and the reaction mixture was stirred for 1 hour under H2 atmosphere (P=1 atm). The catalyst was filtered off and the solvent removed under reduced pressure. The residue was purified by flash chromatography on silica gel (SNAP 10 g) eluting from 75:25 to 40:60 cyclohexane/ethyl acetate affording the title compound (80 mg) as white solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed under reduced pressure
  3. customThe residue was purified by flash chromatography on silica gel (SNAP 10 g)
  4. washeluting from 75:25 to 40:60 cyclohexane/ethyl acetate affording the title compound (80 mg) as white solid

Sources & evidence

ORD record
ord-ef5e3b8522a74378aea91d10e7a80dd7
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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