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Trifluoroacetic anhydride → HCID 66735500, compound

HRID 2047137
Notes
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Reaction equation

HRID 2047137 reaction equation
OOS([O-])=O.[K+].FC(F)(F)C(OC(=O)C(F)(F)F)=[O:10].[C:20]([C:23]1[C:24]([CH:61]2[CH2:66][CH2:65][N:64](C(OC(C)(C)C)=O)[CH2:63][CH2:62]2)=[N:25][C:26]2[N:27]([N:46]=[CH:47][C:48]=2[C:49]2[CH:50]=[N:51][C:52]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)=[CH:53][CH:54]=2)[C:28]=1[N:29](COCC[Si](C)(C)C)COCC[Si](C)(C)C)(=[O:22])[CH3:21].C1(I)C=CC=CC=1>C(#N)C.O>[NH2:29][C:28]1[N:27]2[N:46]=[CH:47][C:48]([C:49]3[CH:50]=[N:51][C:52]([C:55]4[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=4)=[CH:53][CH:54]=3)=[C:26]2[N:25]=[C:24]([CH:61]2[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]2)[C:23]=1[C:20](=[O:22])[CH2:21][OH:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 9845Trifluoroacetic anhydrideHCID 11575IodobenzeneHCID 23707502Potassium hydroxy sulfiteHCID 67494585HCID 67494585, compound

Product 1

HCID 66735500HCID 66735500, compoundYield 19.5%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6342AcetonitrileSolvent

Procedure

A solution of oxone (1.9 g, 3.1 mmol), trifluoroacetic anhydride (1.1 ml, 7.9 mmol) and H2O (5.7 ml) was stirred at 40° C. for 7 h, and then cooled to room temperature. To this a solution of tert-butyl 4-(6-acetyl-7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1-carboxylate (0.87 g, 1.13 mmol) and PhI (0.03 ml, 0.23 mmol) in acetonitrile (17 ml) was added. The resulting solution was stirred at 90° C. for 15 h. On cooling, the reaction mixture was filtered and solids were washed with DCM. It was then concentrated in vacuo to give a crude product which was submitted to the analytical group for purification to afford the desired 1-(7-amino-3-(6-phenylpyridin-3-yl)-5-(piperidin-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyethanone (94.2 mg, 17%).

Workup

  1. temperatureOn cooling
  2. filtrationthe reaction mixture was filtered
  3. washsolids were washed with DCM
  4. concentrationIt was then concentrated in vacuo
  5. customto give a crude product which
  6. customwas submitted to the analytical group for purification

Sources & evidence

ORD record
ord-d12c14484b0a4b59aa57732f47ac91d7
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08591943B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes