Trifluoroacetic acid → Trifluoroacetic acid

HRID 2209220Notes

Reaction equation

HRID 2209220 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[N:10]=[C:11]([O:19][C@@H:20]([C@@H:22]3[CH2:26][C:25](=[O:27])[NH:24][CH2:23]3)[CH3:21])[C:12]3[N:13]([N:15]=[CH:16][C:17]=3[CH3:18])[CH:14]=2)[CH:6]=[CH:5][C:4]=1[N:28]1[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]1.[C:41]([OH:47])([C:43]([F:46])([F:45])[F:44])=[O:42]>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[N:10]=[C:11]([O:19][C@@H:20]([C@H:22]3[CH2:23][NH:24][C:25](=[O:27])[CH2:26]3)[CH3:21])[C:12]3[N:13]([N:15]=[CH:16][C:17]=3[CH3:18])[CH:14]=2)[CH:6]=[CH:5][C:4]=1[N:28]1[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]1.[F:44][C:43]([F:46])([F:45])[C:41]([OH:47])=[O:42]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117842905tert-butyl 4-(2-methoxy-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 526.2%HCID 117843210(R)-4-((R)-1-((6-(3-methoxy-4-(piperazin-1-yl)phenyl)-3-methylpyrazolo[1,5-a]pyrazin-4-yl)oxy)ethyl)pyrrolidin-2-one

Procedure

tert-butyl 4-(2-methoxy-4-(3-methyl-4-((R)-1-((R)-5-oxopyrrolidin-3-yl)ethoxy)pyrazolo[1,5-a]pyrazin-6-yl)phenyl)piperazine-1-carboxylate 5.59 (35 mg, 0.06 mmol) was dissolved in TFA (2.5 mL, 32.7 mmol) and mixture was stirred at room temperature. After 2 hours, reaction mixture was concentrated and azeotroped with toluene to yield (R)-4-((R)-1-((6-(3-methoxy-4-(piperazin-1-yl)phenyl)-3-methylpyrazolo[1,5-a]pyrazin-4-yl)oxy)ethyl)pyrrolidin-2-one 5.60 as a trifluoroacetic acid salt (36 mg).

Workup

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

Sources & evidence

ORD record
ord-2bf04a2f47314df591dcbd16b3c067a6
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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