Trifluoroacetic acid → (S)-N1-(5-(isoquinolin-6-yl)-1,3,4-oxadiazol-2-yl)-3-(4-(trifluoromethyl)phenyl)propane-1,2-diamine

HRID 598815Notes

Reaction equation

HRID 598815 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[O:15][C:14]([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)=[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>[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:14]1[O:15][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)=[N:12][N:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68372994tert-Butyl(S)-1-(5-(isoquinolin-6-yl)-1,3,4-oxadiazol-2-ylamino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

Product 1

HCID 25175218(S)-N1-(5-(isoquinolin-6-yl)-1,3,4-oxadiazol-2-yl)-3-(4-(trifluoromethyl)phenyl)propane-1,2-diamineYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl(S)-1-(5-(isoquinolin-6-yl)-1,3,4-oxadiazol-2-ylamino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate (0.04 g, 0.078 mmol) was treated with 2 mL TFA in 2 mL DCM for 30 minutes. After removing the solvent, the remaining residue was made basic with 2M ammonia in MeOH and loaded on a preparative TLC plate. The TLC plate was developed with 5% 2M ammonia in MeOH in DCM. A white solid was obtained as the desired product (20 mg, 63%). LCMS (API-ES) m/z (%): 414.0 (100%, M++H); 1H NMR (400 MHz, CD3OD) δ ppm 2.72 (dd, J=13.60, 7.53 Hz, 1H) 2.94 (dd, J=13.50, 5.28 Hz, 1H) 3.30-3.37 (m, 2H) 3.39-3.45 (m, 1H) 7.43 (d, J=8.02 Hz, 2H) 7.56 (d, J=8.22 Hz, 2H) 7.87 (d, J=5.87 Hz, 1H) 8.10-8.15 (m, 1H) 8.16-8.20 (m, 1H) 8.34 (s, 1H) 8.47 (d, J=5.87 Hz, 1H) 9.24 (s, 1H).

Workup

  1. customAfter removing the solvent

Sources & evidence

ORD record
ord-6f8913121e10438aa510ac8e59b10a90
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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