(R)-4-((R)-1-((6-(1-(tert-butyl)-1H-pyrazol-4-yl)-2-methylpyrazolo[1,5-a]pyridin-4-yl)oxy)ethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one → example 6.60 on page 587 of WO15017610

HRID 2209263Notes

Reaction equation

HRID 2209263 reaction equation
[C:1]([N:5]1[CH:9]=[C:8]([C:10]2[CH:11]=[C:12]([O:20][C@@H:21]([C@H:23]3[CH2:27][N:26]([C@@H](C4C=CC(OC)=CC=4)C)[C:25](=[O:38])[CH2:24]3)[CH3:22])[C:13]3[N:14]([N:16]=[C:17]([CH3:19])[CH:18]=3)[CH:15]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]>C(O)(C(F)(F)F)=O.C(OCC)(=O)C>[C:1]([N:5]1[CH:9]=[C:8]([C:10]2[CH:11]=[C:12]([O:20][C@@H:21]([C@H:23]3[CH2:27][NH:26][C:25](=[O:38])[CH2:24]3)[CH3:22])[C:13]3[N:14]([N:16]=[C:17]([CH3:19])[CH:18]=3)[CH:15]=2)[CH:7]=[N:6]1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 117843934(R)-4-((R)-1-((6-(1-(tert-butyl)-1H-pyrazol-4-yl)-2-methylpyrazolo[1,5-a]pyridin-4-yl)oxy)ethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one

Product 1

HCID 91886047example 6.60 on page 587 of WO15017610Yield 81.1%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (R)-4-((R)-1-((6-(1-(tert-butyl)-1H-pyrazol-4-yl)-2-methylpyrazolo[1,5-a]pyridin-4-yl)oxy)ethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one (5 mg) in TFA (2 mL) was heated at 60° C. for overnight, cooled to rt. and then removed TFA under vaco., the residue was diluted with ethyl acetate, and washed with brine, dried, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to provide 3 mg of (R)-4-((R)-1-((6-(1-(tert-butyl)-1H-pyrazol-4-yl)-2-methylpyrazolo[1,5-a]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one 6.60.

Workup

  1. washwashed with brine
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3ddba31a53c4464d8e4c65eb3cdd000a
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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