Trifluoroacetic acid → N-(4-(3-fluorophenyl)piperidin-3-yl)-3-(pyridin-4-yl)-1H-indazole-5-carboxamide

HRID 1467322Notes

Reaction equation

HRID 1467322 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:10]=[C:11]([CH:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH:16]2[NH:28][C:29]([C:31]2[CH:32]=[C:33]3[C:37](=[CH:38][CH:39]=2)[N:36](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:35]=[C:34]3[C:59]2[CH:64]=[CH:63][N:62]=[CH:61][CH:60]=2)=[O:30])[CH:12]=[CH:13][CH:14]=1>C([SiH](CC)CC)C>[F:8][C:9]1[CH:10]=[C:11]([CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH:16]2[NH:28][C:29]([C:31]2[CH:32]=[C:33]3[C:37](=[CH:38][CH:39]=2)[NH:36][N:35]=[C:34]3[C:59]2[CH:60]=[CH:61][N:62]=[CH:63][CH:64]=2)=[O:30])[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67996977tert-butyl 4-(3-fluorophenyl)-3-(3-(pyridin-4-yl)-1-trityl-1H-indazole-5-carboxamido)piperidine-1-carboxylate

Product 1

HCID 67996351N-(4-(3-fluorophenyl)piperidin-3-yl)-3-(pyridin-4-yl)-1H-indazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 12052TriethylsilaneCatalyst

Procedure

Trifluoroacetic acid (1 mL) was added to tert-butyl 4-(3-fluorophenyl)-3-(3-(pyridin-4-yl)-1-trityl-1H-indazole-5-carboxamido)piperidine-1-carboxylate (0.105 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-2068c79e30ba4f64a0c32cbb25799f4c
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

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