Trifluoroacetic acid → (2S)-1-(4-(Isoquinolin-6-yl)-1H-pyrazol-1-yl)-3-(4-(trifluoromethyl)phenyl)-propan-2-amine

HRID 598899Notes

Reaction equation

HRID 598899 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][C@@H:17]([NH:29]C(=O)OC(C)(C)C)[CH2:18][C:19]4[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=4)[CH:15]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][C@@H:17]([NH2:29])[CH2:18][C:19]4[CH:20]=[CH:21][C:22]([C:25]([F:27])([F:26])[F:28])=[CH:23][CH:24]=4)[CH:15]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57950543tert-butyl(S)-3-(4-(isoquinolin-6-yl)-1H-pyrazol-1-yl)-1-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

Product 1

HCID 57950501(2S)-1-(4-(Isoquinolin-6-yl)-1H-pyrazol-1-yl)-3-(4-(trifluoromethyl)phenyl)-propan-2-amineYield 57.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl(S)-3-(4-(isoquinolin-6-yl)-1H-pyrazol-1-yl)-1-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate (90 mg, 0.18 mmol) and TFA (5.00 mL, 64 mmol) in DCM (5 mL) was stirred at room temperature for 2 hours. After concentration by vacuum distillation, the residue was purified by reverse-phase HPLC (Phenomenex Synergi 4m Max RP 80 A column, 150×21 mm, 20 mL/min, 10-95% CH3CN/H2O, 0.1% TFA, 10.5 minute gradient) to give the product as an off-white solid (41 mg, 57%). HRMS (TOF) Calcd for C22H20F3N4+: 397.1635, found: 397.1642.

Workup

  1. concentrationAfter concentration
  2. distillationby vacuum distillation
  3. customthe residue was purified by reverse-phase HPLC (Phenomenex Synergi 4m Max RP 80 A column, 150×21 mm, 20 mL/min, 10-95% CH3CN/H2O, 0.1% TFA, 10.5 minute gradient)

Sources & evidence

ORD record
ord-e24c291992a54eb3b6f4a6dfe6aa5ae9
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

Loading…