HCID 117843199, compound → (R)-4-((R)-1-((6-chloro-3-methylpyrazolo[1,5-a]pyrazin-4-yl)oxy)ethyl)pyrrolidin-2-one
Reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([O:12][C@@H:13]([C@H:15]2[CH2:19][N:18]([C@@H](C3C=CC(OC)=CC=3)C)[C:17](=[O:30])[CH2:16]2)[CH3:14])[C:5]2[N:6]([N:8]=[CH:9][C:10]=2[CH3:11])[CH:7]=1>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[N:3]=[C:4]([O:12][C@@H:13]([C@H:15]2[CH2:19][NH:18][C:17](=[O:30])[CH2:16]2)[CH3:14])[C:5]2[N:6]([N:8]=[CH:9][C:10]=2[CH3:11])[CH:7]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
(R)-4-((R)-1-(6-chloro-3-methylpyrazolo[1,5-a]pyrazin-4-yloxy)ethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one 5.53 (31 mg, 0.07 mmol) was dissolved in 1.5 mL of TFA and mixture was heated at 60° C. After 17 hours, reaction mixture was cooled to rt and concentrated under reduced pressure. Resulting residue was taken up in ethyl acetate and washed with sat NaHCO3 (aq). Layers were separated and aqueous was extracted with ethyl acetate. Combined organics were washed with 1:1 sat. NaHCO3 (aq)/brine, dried, filtered, and concentrated under reduced pressure to yield (R)-4-((R)-1-((6-chloro-3-methylpyrazolo[1,5-a]pyrazin-4-yl)oxy)ethyl)pyrrolidin-2-one 5.54 (21 mg), which was used without further purification.
Workup
- customreaction mixture
- temperaturewas cooled to rt
- concentrationconcentrated under reduced pressure
- washwashed
- customLayers were separated
- extractionaqueous was extracted with ethyl acetate
- washCombined organics were washed with 1:1 sat. NaHCO3 (aq)/brine
- customdried
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-886c2693e3bf44af950702976df438f6
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376441B2
Reaction notes
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