Trifluoroacetic acid → Trifluoroacetic acid

HRID 2209207Notes

Reaction equation

HRID 2209207 reaction equation
[O:1]=[C:2]1[NH:6][CH2:5][C@H:4]([C@H:7]([O:9][C:10]2[C:11]3[N:12]([N:35]=[CH:36][CH:37]=3)[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]4)=[CH:18][CH:17]=3)[N:15]=2)[CH3:8])[CH2:3]1.[C:38]([OH:44])([C:40]([F:43])([F:42])[F:41])=[O:39]>>[N:22]1([C:19]2[CH:18]=[CH:17][C:16]([C:14]3[N:15]=[C:10]([O:9][C@@H:7]([C@H:4]4[CH2:5][NH:6][C:2](=[O:1])[CH2:3]4)[CH3:8])[C:11]4[N:12]([N:35]=[CH:36][CH:37]=4)[CH:13]=3)=[CH:21][CH:20]=2)[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]1.[F:41][C:40]([F:43])([F:42])[C:38]([OH:44])=[O:39]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117843609HCID 117843609, compound

Product 2

HCID 6422Trifluoroacetic acidYield 359.6%HCID 117843122HCID 117843122, compound

Procedure

tert-butyl 4-(4-(4-((R)-1-((R)-5-oxopyrrolidin-3-yl)ethoxy)pyrazolo[1,5-a]pyrazin-6-yl)phenyl)piperazine-1-carboxylate 5.43 (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-(4-(piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrazin-4-yl)oxy)ethyl)pyrrolidin-2-one 5.44 as a trifluroacetic acid salt (41 mg).

Workup

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

Sources & evidence

ORD record
ord-abd8de562bf040d68c9279adc793edb4
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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