Trifluoroacetic acid → 5-phenyl-N-(3-(pyridin-4-yl)-1H-indazol-5-yl)piperidine-3-carboxamide

HRID 1467325Notes

Reaction equation

HRID 1467325 reaction equation
FC(F)(F)C(O)=O.[C:8]1([CH:14]2[CH2:19][CH:18]([C:20](=[O:56])[NH:21][C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[N:27](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:26]=[C:25]4[C:50]3[CH:55]=[CH:54][N:53]=[CH:52][CH:51]=3)[CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C([SiH](CC)CC)C>[C:8]1([CH:14]2[CH2:15][NH:16][CH2:17][CH:18]([C:20]([NH:21][C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[NH:27][N:26]=[C:25]4[C:50]3[CH:51]=[CH:52][N:53]=[CH:54][CH:55]=3)=[O:56])[CH2:19]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66613498tert-butyl 3-phenyl-5-(3-(pyridin-4-yl)-1-trityl-1H-indazol-5-ylcarbamoyl)piperidine-1-carboxylate

Product 1

HCID 569428435-phenyl-N-(3-(pyridin-4-yl)-1H-indazol-5-yl)piperidine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 12052TriethylsilaneCatalyst

Procedure

Trifluoroacetic acid (1 mL) was added to tert-butyl 3-phenyl-5-(3-(pyridin-4-yl)-1-trityl-1H-indazol-5-ylcarbamoyl)piperidine-1-carboxylate (0.117 mmol). The reaction was stirred at room temperature for 30 minutes. Triethylsilane (1 drop) was added to the reaction and stirred for an additional 5 minutes. The reaction was concentrated in vacuo and purified using prep LC/MS.

Workup

  1. stirringstirred for an additional 5 minutes
  2. concentrationThe reaction was concentrated in vacuo
  3. custompurified

Sources & evidence

ORD record
ord-0d3f924d591b485d8380912ec9c1a4a8
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

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