Trifluoroacetic acid → HCID 178434450, compound

HRID 2241229Notes

Reaction equation

HRID 2241229 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:28]2[CH2:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[NH:30][C:29]2=[O:38])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[N:15](CC3C=CC(OC)=CC=3)[N:16]=[C:17]([CH3:18])[C:10]=12.FC(F)(F)C(O)=O>>[F:1][C:2]1[CH:3]=[C:4]([N:28]2[CH2:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[NH:30][C:29]2=[O:38])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[NH:15][N:16]=[C:17]([CH3:18])[C:10]=12

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68514108HCID 68514108, compound

Product 1

HCID 178434450HCID 178434450, compound

Conditions

Temperature
80 °C

Procedure

To a reaction tube were added 3-(3-fluoro-4-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-3,4-dihydroquinazolin-2(1H)-one (17.6 mg, 0.035 mmol) and excess trifluoroacetic acid (0.5 mL). The solution was stirred at 80° C. for 30 minutes in a sealed tube under nitrogen. The reaction mixture was cooled to room temperature and the solvent was evaporated under reduced pressure. The crude residue was triturated with diethylether. The resulting solid was filtered, washed with ether, and dried to afford the desired product as an off-white solid as the mono-TFA salt (12.8 mg, 74%). LRMS (APCI pos) m/e 390.3 (M+1). 1H NMR (400 MHz, DMSO-d6) δ 9.77 (s, 1H), 8.30 (d, J=5.5 Hz, 1H), 7.60 (d, J=12.5 Hz, 1H), 7.50 (t, J=9.0 Hz, 1H), 7.38 (d, J=9.0 Hz, 1H), 7.20 (d, J=7.4 Hz, 2H), 6.96 (t, J=7.0 Hz, 3H), 6.90 (d, J=8.2 Hz, 2H), 6.23 (d, J=5.5 Hz, 1H), 4.89 (s, 2H), 2.64 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. customThe crude residue was triturated with diethylether
  4. filtrationThe resulting solid was filtered
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-ef4f52f9175e49478f0eaf3adf8364dc
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

Loading…