Trifluoroacetic acid → Trifluoroacetic acid

HRID 2209210Notes

Reaction equation

HRID 2209210 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[N:10]=[C:11]([O:18][C@@H:19]([C@@H:21]3[CH2:25][C:24](=[O:26])[NH:23][CH2:22]3)[CH3:20])[C:12]3[N:13]([N:15]=[CH:16][CH:17]=3)[CH:14]=2)[CH:6]=[CH:5][C:4]=1[N:27]1[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]1.[C:40]([OH:46])([C:42]([F:45])([F:44])[F:43])=[O:41]>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[N:10]=[C:11]([O:18][C@@H:19]([C@H:21]3[CH2:22][NH:23][C:24](=[O:26])[CH2:25]3)[CH3:20])[C:12]3[N:13]([N:15]=[CH:16][CH:17]=3)[CH:14]=2)[CH:6]=[CH:5][C:4]=1[N:27]1[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]1.[F:43][C:42]([F:45])([F:44])[C:40]([OH:46])=[O:41]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117843555HCID 117843555, compound

Product 2

HCID 6422Trifluoroacetic acidYield 350.8%HCID 117843062HCID 117843062, compound

Procedure

tert-butyl 4-(2-methoxy-4-(4-((R)-1-((R)-5-oxopyrrolidin-3-yl)ethoxy)pyrazolo[1,5-a]pyrazin-6-yl)phenyl)piperazine-1-carboxylate 5.47 (51 mg, 0.1 mmol) was dissolved in TFA (4 mL, 52.23 mmol) and mixture was stirred at room temperature. After 4 hours, reaction mixture was concentrated and azeotroped with toluene to yield (R)-4-((R)-1-((6-(3-methoxy-4-(piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrazin-4-yl)oxy)ethyl)pyrrolidin-2-one 5.48 as a trifluoroacetic acid salt (40 mg).

Workup

  1. customreaction mixture
  2. concentrationwas concentrated
  3. customazeotroped with toluene

Sources & evidence

ORD record
ord-45da1f881e364b47a33e3454ab23861b
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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