Trifluoroacetic acid → HCID 57950504, compound

HRID 598845Notes

Reaction equation

HRID 598845 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[O:15][N:14]=[C:13]([NH:16][CH2:17][C@@H:18]([NH:30]C(=O)OC(C)(C)C)[CH2:19][C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=4)[CH:12]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl.CCOC(C)=O>[NH2:30][C@@H:18]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:29])[F:28])=[CH:22][CH:21]=1)[CH2:17][NH:16][C:13]1[CH:12]=[C:11]([C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[CH:1]=[N:2][CH:3]=[CH:4]3)[O:15][N:14]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86635690HCID 86635690, compound

Product 1

HCID 57950504HCID 57950504, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl(S)-1-(5-(isoquinolin-6-yl)isoxazol-3-ylamino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate (0.027 g, 0.053 mmol) in 5 mL of DCM was added TFA (0.50 mL, 6.5 mmol). The mixture was stirred for 30 minutes and diluted with 20 mL of EtOAc. The mixture was washed twice with 10 mL of 10% aqueous Na2CO3 and dried over MgSO4. Filtration and concentration under reduced pressure, followed by flash chromatography on silica gel (5% to 10% MeOH/DCM) afforded N-((S)-2-amino-3-(4-(trifluoromethyl)phenyl)propyl)-5-(isoquinolin-6-yl)isoxazol-3-amine (0.013 g, 60% yield) as a clear oil. MS m/z: 413 (M+1); 1H NMR (400 MHz, CD3OD) δ ppm 9.26 (s, 1H), 8.48 (d, J=5.8 Hz, 1H), 8.34 (s, 1H), 8.19 (d, J=8.6 Hz, 1H), 8.01 (dd, J=1.3 Hz, 8.6 Hz, 1H), 7.90 (d, J=5.9 Hz, 1H), 7.62 (d, J=8.2 Hz, 2H), 7.47 (d, J=8.0 Hz, 2H), 6.52 (s, 1H), 3.45-3.25 (m, 2H), 3.34 (s, 2H), 3.18 (dd, J=7.4 Hz, 13.5 Hz, 1H), 3.00 (dd, J=5.5 Hz, 13.5 Hz, 1H), 2.75 (dd, J=7.9 Hz, 13.5 Hz, 1H), 2.22 (dt, 1.8 Hz, 6.7 Hz, 1H).

Workup

  1. washThe mixture was washed twice with 10 mL of 10% aqueous Na2CO3
  2. dry with materialdried over MgSO4
  3. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-915bdbf0f23b4dd995183f9c242c4be2
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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