Trifluoroacetic acid → (2R)-4-(5-(Isoquinolin-6-yl)-1,3,4-oxadiazol-2-yl)-1-(4-(trifluoromethyl)phenyl)butan-2-amine

HRID 598903Notes

Reaction equation

HRID 598903 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[O:15][C:14]([CH2:16][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)=[N: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[O:15][C:14]([CH2:16][CH2:17][C@@H:18]([NH2:30])[CH2:19][C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:29])[F:28])=[CH:22][CH:21]=4)=[N:13][N:12]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57950648tert-Butyl(R)-4-(5-(isoquinolin-6-yl)-1,3,4-oxadiazol-2-yl)-1-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamate

Product 1

HCID 57950640(2R)-4-(5-(Isoquinolin-6-yl)-1,3,4-oxadiazol-2-yl)-1-(4-(trifluoromethyl)phenyl)butan-2-amineYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl(R)-4-(5-(isoquinolin-6-yl)-1,3,4-oxadiazol-2-yl)-1-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamate (0.060 g, 0.12 mmol) was stirred with 10 mL TFA in 10 mL DCM for 1 hour. After removing the solvent, the remaining residue was made basic with 2 M ammonia in MeOH and purified by chromatography on silica gel (4% 2M ammonia MeOH solution in DCM) to give the desired product as a white solid (0.045 g, 93%). LCMS (API-ES) m/z: 413 (M+H+); 1H NMR (400 MHz, CD3OD) δ ppm 1.87-1.97 (m, 1H), 2.17-2.27 (m, 1H), 2.63-2.79 (m, 2H), 2.91-2.98 (m, 1H), 3.12 (dd, J=13.40, 5.18 Hz, 1H), 4.18-4.25 (m, 1H), 7.50 (d, J=8.02 Hz, 2H), 7.64 (d, J=8.02 Hz, 2H), 7.92 (d, J=5.67 Hz, 1H), 8.14-8.19 (m, 1H), 8.22-8.27 (m, 1H), 8.50 (d, J=5.48 Hz, 1H), 9.30 (s, 1H), one H was obscured.

Workup

  1. customAfter removing the solvent
  2. custompurified by chromatography on silica gel (4% 2M ammonia MeOH solution in DCM)

Sources & evidence

ORD record
ord-ad4077d5b71f42788f9e2ca76a359a59
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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