(R)-4-((R)-1-(6-chloro-3-methyl-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one → (R)-4-((R)-1-((6-chloro-3-methyl-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one

HRID 2208994Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([O:8][C@@H:9]([C@H:11]2[CH2:15][N:14]([C@@H](C3C=CC(OC)=CC=3)C)[C:13](=[O:26])[CH2:12]2)[CH3:10])[C:5]2[N:27]([CH3:30])[CH:28]=[N:29][C:4]=2[CH:3]=1>FC(F)(F)C(O)=O>[Cl:1][C:2]1[N:7]=[C:6]([O:8][C@@H:9]([C@H:11]2[CH2:15][NH:14][C:13](=[O:26])[CH2:12]2)[CH3:10])[C:5]2[N:27]([CH3:30])[CH:28]=[N:29][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 57.5 °C

Procedure

(R)-4-((R)-1-(6-chloro-3-methyl-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one 2.05 (32 mg, 0.075 mmol) was dissolved in trifluoroacetic acid (1.1 mL) at room temperature and mixture was heated between 55-60° C. overnight. After cooling to room temperature, mixture was concentrated under reduced pressure, taken up in ethyl acetate, washed with saturated NaHCO3 (aq), and layers separated. Aqueous layer was extracted with ethyl acetate (3×) and combined organic layers were washed with 1:1 saturated NaHCO3 (aq): brine, dried (Na2SO4), filtered, and concentrated under reduced pressure to yield (R)-4-((R)-1-(6-chloro-3-methyl-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)pyrrolidin-2-one 2.06, which was used without further purification.

Workup

temperatureAfter cooling to room temperature
concentrationmixture was concentrated under reduced pressure
washwashed with saturated NaHCO3 (aq), and layers
customseparated
extractionAqueous layer was extracted with ethyl acetate (3×)
washwere washed with 1:1 saturated NaHCO3 (aq)
dry with materialbrine, dried (Na2SO4)
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-d3c10eeda7184efcb4e3eda952b3a0d5
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376441B2

Reaction notes

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