Trifluoroacetic acid → N-[(3R)-1-phenylpiperidin-3-yl]-3-(pyridin-4-yl)-1H-indazole-5-carboxamide

HRID 1467312Notes

Reaction equation

HRID 1467312 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][CH2:10][C@@H:9]([NH:13][C:14]([C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[N:21](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:20]=[C:19]4[C:44]3[CH:49]=[CH:48][N:47]=[CH:46][CH:45]=3)=[O:15])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>CS(C)=O>[C:1]1([N:7]2[CH2:12][CH2:11][CH2:10][C@@H:9]([NH:13][C:14]([C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][N:20]=[C:19]4[C:44]3[CH:45]=[CH:46][N:47]=[CH:48][CH:49]=3)=[O:15])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 12052TriethylsilaneHCID 67995889N-[(3R)-1-phenylpiperidin-3-yl]-3-(pyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide

Product 1

HCID 70652207N-[(3R)-1-phenylpiperidin-3-yl]-3-(pyridin-4-yl)-1H-indazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Crude N-[(3R)-1-phenylpiperidin-3-yl]-3-(pyridin-4-yl)-1-trityl-1H-indazole-5-carboxamide (129 mg, 0.202 mmol) was stirred with TFA (0.5 ml) at room temperature for 45 minutes. Addition TFA (1 ml) was added and the reaction mixture was stirred at room temperature for 1.5 hours. Triethylsilane (100 μl, 0.626 mmol) was added and then the reaction mixture diluted with DMSO purified by mass-triggered reverse-phase HPLC to provide N-[(3R)-1-phenylpiperidin-3-yl]-3-(pyridin-4-yl)-1H-indazole-5-carboxamide.

Workup

  1. additionwas added
  2. custompurified by mass-triggered reverse-phase HPLC

Sources & evidence

ORD record
ord-515976d4bd60490485f1e1e4a1d0ddc1
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

Loading…