Trifluoroacetic acid → HCID 46836618, compound
Reaction equation
COC1C=CC(C[N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][CH:17]([NH:21][C:22]([NH:24][C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)=[O:23])[CH2:18][CH2:19][C:20]=4[C:11]=3[CH:10]=[N:9]2)=CC=1.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[C:25]1([NH:24][C:22]([NH:21][CH:17]2[CH2:16][C:15]3[CH:14]=[N:13][C:12]4[NH:8][N:9]=[CH:10][C:11]=4[C:20]=3[CH2:19][CH2:18]2)=[O:23])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
To 1-[3-(4-methoxy-benzyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinolin-7-yl]-3-phenyl-urea (0.093 g, 0.217 mmol) was added trifluoroacetic acid (1 mL). The reaction mixture was heated at 65° C. for 16 hours. On completion of the reaction, toluene (2 mL) was added and the solvent removed under reduced pressure. The crude product was purified using reverse phase HPLC to give the desired product, 1-phenyl-3-(6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c]isoquinolin-7-yl)urea as an off-white solid (0.030 g, 45%). M.p.>216° C.; 400 MHz 1H NMR (DMSO-d6) δ: 13.38 (s, 1H), 8.34 (s, 1H), 8.01 (s, 1H), 7.94 (s, 1H), 7.36 (d, J=8.0 Hz, 2H), 7.21 (dd, J1=J2=8.0 Hz, 2H), 6.88 (dd, J1=J2=8.0 Hz, 2H), 6.31 (d, J=8.0 Hz, 1H), 4.04 (m, 1H), 3.19 (m, 1H), 3.05 (m, 2H), 2.80 (m, 1H), 2.10 (m, 1H), 1.88 (m, 1H); LCMS [M+H]: 308.