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Trifluoroacetic acid → (S)-3-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-(2-hydroxyethyl)-4-isopropylimidazolidin-2-one

HRID 539031
Notes
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Reaction equation

HRID 539031 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][C@H:7]([CH:9]([CH3:11])[CH3:10])[N:6]([C:12]2[CH:17]=[CH:16][N:15]3[N:18]=[CH:19][C:20]([C:21]4[CH:26]=[CH:25][C:24]([C:27]5[N:31]=[CH:30][N:29](COCC[Si](C)(C)C)[N:28]=5)=[CH:23][CH:22]=4)=[C:14]3[N:13]=2)[C:5]1=[O:40].FC(F)(F)C(O)=O.[OH-].[Na+].CO>>[NH:29]1[CH:30]=[N:31][C:27]([C:24]2[CH:23]=[CH:22][C:21]([C:20]3[CH:19]=[N:18][N:15]4[CH:16]=[CH:17][C:12]([N:6]5[C@@H:7]([CH:9]([CH3:11])[CH3:10])[CH2:8][N:4]([CH2:3][CH2:2][OH:1])[C:5]5=[O:40])=[N:13][C:14]=34)=[CH:26][CH:25]=2)=[N:28]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 23721981Sodium hydroxide methanolHCID 67034260(S)-1-(2-hydroxyethyl)-4-isopropyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one

Product 1

HCID 178448149(S)-3-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-(2-hydroxyethyl)-4-isopropylimidazolidin-2-oneYield 4.4%

Procedure

To (S)-1-(2-hydroxyethyl)-4-isopropyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)imidazolidin-2-one (0.18 g, 0.32 mmol) was added trifluoroacetic acid (5 mL) and the reaction was stirred at ambient temperature for 3 hours. The reaction was concentrated in vacuo and the material purified by reverse preparative HPLC to yield the crude product and the corresponding trifluoroacetate ester. To this material was added 1N NaOH/MeOH and the mixture stirred at ambient temperature for 2 hours. The mixture was concentrated in vacuo. The combined crude product was purified by reverse preparative HPLC to give (S)-3-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-(2-hydroxyethyl)-4-isopropylimidazolidin-2-one (0.0061 g, 0.014 mmol, 4.4% yield) as the mono TFA salt. LCMS (APCI+) m/z 433 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe material purified by reverse preparative HPLC
  3. customto yield the crude product
  4. stirringthe mixture stirred at ambient temperature for 2 hours
  5. concentrationThe mixture was concentrated in vacuo
  6. customwas purified by reverse preparative HPLC

Sources & evidence

ORD record
ord-85d3a62cbb0b476ca8957105d21161bb
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08865726B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes