Trifluoroacetic acid → (2R)-4-(3-(isoquinolin-6-yl)isoxazol-5-yl)-1-phenylbutan-2-amine

HRID 598852Notes

Reaction equation

HRID 598852 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[CH:15]=[C:14]([CH2:16][CH2:17][C@@H:18]([NH:26]C(=O)OC(C)(C)C)[CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[O:13][N:12]=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:15]=[C:14]([CH2:16][CH2:17][C@@H:18]([NH2:26])[CH2:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[O:13][N:12]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57950728tert-Butyl(R)-4-(3-(isoquinolin-6-yl)isoxazol-5-yl)-1-phenylbutan-2-ylcarbamate

Product 1

HCID 57950666(2R)-4-(3-(isoquinolin-6-yl)isoxazol-5-yl)-1-phenylbutan-2-amineYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl(R)-4-(3-(isoquinolin-6-yl)isoxazol-5-yl)-1-phenylbutan-2-ylcarbamate (0.089 g, 0.20 mmol) in 5 mL of DCM was added 1 mL of TFA. After 30 minutes, the solvent was removed by rotary evaporation. The residue was taken up in 2 N NH3/MeOH to free base the amine. Concentration under reduced pressure, followed by flash chromatography on silica gel (5% to 10% MeOH/DCM) afforded (2R)-4-(3-(isoquinolin-6-yl)isoxazol-5-yl)-1-phenylbutan-2-amine (0.015 g, 22% yield) as a brown solid. MS m/z: 344 (M+1); 1H NMR (400 MHz, CD3OD) δ ppm 9.46 (s, 1H), 8.58-8.55 (m, 1H), 8.48 (s, 1H), 8.35-8.25 (m, 2H), 8.12 (d, J=6.2 Hz, 1H), 7.40-7.27 (m, 5H), 6.79 (s, 1H), 3.61-3.50 (m, 2H), 3.19-2.94 (m, 3H), 2.16-2.03 (m, 2H).

Workup

  1. customthe solvent was removed by rotary evaporation
  2. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-a2eadc2ee402428b80c2d6688b04fda5
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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