Trifluoroacetic acid → Trifluoroacetic acid

HRID 2209217Notes

Reaction equation

HRID 2209217 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]4)=[CH:13][CH:12]=3)[N:8]=[C:7]([O:30][C@@H:31]([C@@H:33]3[CH2:37][C:36](=[O:38])[NH:35][CH2:34]3)[CH3:32])[C:6]=12.[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40]>>[CH3:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]4)=[CH:13][CH:12]=3)[N:8]=[C:7]([O:30][C@@H:31]([C@H:33]3[CH2:34][NH:35][C:36](=[O:38])[CH2:37]3)[CH3:32])[C:6]=12.[F:42][C:41]([F:44])([F:43])[C:39]([OH:45])=[O:40]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117843441tert-butyl 4-(4-(3-methyl-4-((R)-1-((R)-5-oxopyrrolidin-3-yl)ethoxy)pyrazolo[1,5-a]pyrazin-6-yl)phenyl)piperazine-1-carboxylate

Product 2

HCID 6422Trifluoroacetic acidYield 460.4%HCID 117843436(R)-4-((R)-1-((3-methyl-6-(4-(piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrazin-4-yl)oxy)ethyl)pyrrolidin-2-one

Procedure

tert-butyl 4-(4-(3-methyl-4-((R)-1-((R)-5-oxopyrrolidin-3-yl)ethoxy)pyrazolo[1,5-a]pyrazin-6-yl)phenyl)piperazine-1-carboxylate (20.2 mg, 0.04 mmol) 5.55 was dissolved in TFA (1.5 mL, 20 mmol) and mixture stirred at room temperature. After 2 hours, reaction mixture was concentrated and azeotroped with toluene to yield (R)-4-((R)-1-((3-methyl-6-(4-(piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrazin-4-yl)oxy)ethyl)pyrrolidin-2-one 5.56 as a trifluoroacetic acid salt (21 mg).

Workup

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

Sources & evidence

ORD record
ord-445861a4a4af4f26b4bae4e49afe8328
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

Loading…