HCID 178434031, compound → HCID 178434428, compound

HRID 253263Notes

Reaction equation

HRID 253263 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:16]2[C:25]3[C:24]([F:26])=[CH:23][C:22]([OH:27])=[C:21]([F:28])[C:20]=3[C:19]3[C:29]([CH3:36])=[N:30][N:31](C(C)(C)C)[C:18]=3[N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8]CC1C=CC=CC=1>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:16]2[C:25]3[C:24]([F:26])=[CH:23][C:22]([OH:27])=[C:21]([F:28])[C:20]=3[C:19]3[C:29]([CH3:36])=[N:30][NH:31][C:18]=3[N:17]=2)[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

3

Reactant 1

HCID 178434031HCID 178434031, compound

Product 1

HCID 178434428HCID 178434428, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

5-{3-Chloro-4-[(phenylmethyl)oxy]phenyl}-3-(1,1-dimethylethyl)-6,9-difluoro-1-methyl-3H-pyrazolo[3,4-c]isoquinolin-8-ol (0.010 g, 0.020 mmol) was dissolved in trifluoroacetic acid (0.5 mL) and stirred at room temperature for 1.3 h, then at 50° C. for 0.2 h and finally at 60° C. for 0.5 h. The mixture was then concentrated in vacuo to afford a residue which was purified by preparative HPLC to afford 5-(3-chloro-4-hydroxyphenyl)-6,9-difluoro-1-methyl-3H-pyrazolo[3,4-c]isoquinolin-8-ol as a yellow solid (0.0047 g, 0.013 mmol, 66% yield). 1H NMR (400 MHz, CD3OD): 7.47 (t, 1H), 7.28 (dt, 1H), 6.98 (d, 1H), 6.86 (dd, 1H), 2.82 (d, 3H); MS (EI) for C17H10ClF2N3O2: 362 (MH+), 394 (MNa+), 400 (MK+).

Workup

  1. waitat 50° C. for 0.2 h
  2. waitfinally at 60° C. for 0.5 h
  3. concentrationThe mixture was then concentrated in vacuo
  4. customto afford a residue which
  5. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-dafb6882baa248b58139c393bff18457
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

Loading…