Trifluoroacetic acid → (R)-5-(1-(piperidin-3-yl)-1H-1,2,3-triazol-4-yl)-3-(pyridin-4-yl)-1H-indazole

HRID 1465694Notes

Reaction equation

HRID 1465694 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([N:14]2[CH:18]=[C:17]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[N:24](C(OC(C)(C)C)=O)[N:23]=[C:22]4[C:35]3[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=3)[N:16]=[N:15]2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([N:14]2[CH:18]=[C:17]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[NH:24][N:23]=[C:22]4[C:35]3[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=3)[N:16]=[N:15]2)[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86695575(R)-tert-butyl 5-(1-(1-(tert-butoxycarbonyl)piperidin-3-yl)-1H-1,2,3-triazol-4-yl)-3-(pyridin-4-yl)-1H-indazole-1-carboxylate

Product 1

HCID 86695576(R)-5-(1-(piperidin-3-yl)-1H-1,2,3-triazol-4-yl)-3-(pyridin-4-yl)-1H-indazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the crude (R)-tert-butyl 5-(1-(1-(tert-butoxycarbonyl)piperidin-3-yl)-1H-1,2,3-triazol-4-yl)-3-(pyridin-4-yl)-1H-indazole-1-carboxylate in CH2Cl2 (40 mL), added TFA (2.5 mL) and stirred at room temperature overnight under a stream of nitrogen. Evaporated the solvents and column purified (5-10% MeOH in CH2Cl2) to give (R)-5-(1-(piperidin-3-yl)-1H-1,2,3-triazol-4-yl)-3-(pyridin-4-yl)-1H-indazole (0.4 g).

Workup

  1. customEvaporated the solvents and column
  2. custompurified (5-10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-85c8c2cc2036400ebcb01c14259069d8
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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