HCID 131735973, compound → HCID 178488438, compound

HRID 2209033Notes

Reaction equation

HRID 2209033 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([O:17][C@@H:18]([C@H:20]3[CH2:24][N:23]([C@@H](C4C=CC(OC)=CC=4)C)[C:22](=[O:35])[CH2:21]3)[CH3:19])[C:14]3[N:36](COCC[Si](C)(C)C)[C:37]([CH3:39])=[N:38][C:13]=3[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]>C(O)(C(F)(F)F)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([O:17][C@@H:18]([C@H:20]3[CH2:24][NH:23][C:22](=[O:35])[CH2:21]3)[CH3:19])[C:14]3[NH:36][C:37]([CH3:39])=[N:38][C:13]=3[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

3

Reactant 1

HCID 131735973HCID 131735973, compound

Product 1

HCID 178488438HCID 178488438, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
60 °C

Procedure

(R)-4-((R)-1-(6-(3,4-dimethoxyphenyl)-2-methyl-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one was dissolved in TFA. Reaction was heated to 60° C. After 6 h, reaction was cooled to r.t. and was concentrated in vacuo. The resulting residue was diluted with EtOAc, brine, and saturated NaHCO3. The phases were separated, and the aqueous phase was extracted with EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated to afford (R)-4-((R)-1-(6-(3,4-dimethoxyphenyl)-2-methyl-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)pyrrolidin-2-one 2.66 that was used without further purification. [M+H]+ calcd C21H24N4O4: 397.18; found 397.1.

Workup

  1. customReaction
  2. customreaction
  3. temperaturewas cooled to r.t.
  4. concentrationwas concentrated in vacuo
  5. additionThe resulting residue was diluted with EtOAc, brine, and saturated NaHCO3
  6. customThe phases were separated
  7. extractionthe aqueous phase was extracted with EtOAc
  8. dry with materialThe organic layer was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d00ff15e82634abc93d4420c406702a7
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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