Trifluoroacetic acid → HCID 46836618, compound

HRID 2383476Notes

Reaction equation

HRID 2383476 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]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59490421HCID 59490421, compound

Product 1

HCID 46836618HCID 46836618, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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.

Workup

  1. additionwas added
  2. customthe solvent removed under reduced pressure
  3. customThe crude product was purified

Sources & evidence

ORD record
ord-038d9b44920242918e1ada543bb74c10
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

Loading…