Trifluoroacetic acid → HCID 25175220, compound

HRID 598821Notes

Reaction equation

HRID 598821 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[N: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)[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[N: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)[O:13][N:12]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86635687HCID 86635687, compound

Product 1

HCID 25175220HCID 25175220, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl(R)-4-(3-(isoquinolin-6-yl)-1,2,4-oxadiazol-5-yl)-1-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamate (0.016 g, 0.03 mmol) was treated with TFA (1 mL, 13 mmol) in 1 mL DCM for 1 hour. After removing the solvent and making the remaining residue basic with 2M ammonia in MeOH, the residue was subjected to a silica gel plug using 3% 2M ammonia in MeOH in DCM as the eluant to yield an off-white solid as the desired product. LCMS (API-ES) m/z (%): 413.0 (100%, M++H); 1H NMR (400 MHz, CD3OD) δ ppm 2.07-2.18 (m, 1H) 2.22 (s, 1H) 2.95-3.03 (m, 1H) 3.05-3.13 (m, 1H) 3.17-3.28 (m, 2H) 3.48-3.58 (m, 1H) 7.52 (d, J=7.53 Hz, 2H) 7.68 (d, J=8.03 Hz, 2H) 7.95 (d, J=5.52 Hz, 1H) 8.23-8.31 (m, 2H) 8.54 (d, J=6.02 Hz, 1H) 8.64 (s, 1H) 9.33 (s, 1H).

Workup

  1. customAfter removing the solvent

Sources & evidence

ORD record
ord-a080e1a50d73442ea9b414aa9fc6d524
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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