Hydrochloric Acid → HCID 178486395, compound

HRID 253235Notes

Reaction equation

HRID 253235 reaction equation
FC(F)(F)C(O)=O.C(=O)([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:30]3[CH:29]=[C:28]([O:31][CH3:32])[C:27]([O:33][CH2:34][CH:35]4[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]4)=[CH:26][C:25]=3[C:24]3[C:42]([CH3:45])=[N:43][NH:44][C:23]=3[N:22]=2)=[CH:17][CH:16]=1)OC(C)(C)C.[ClH:47]>O1CCOCC1>[ClH:47].[CH3:45][C:42]1[C:24]2[C:25]3[CH:26]=[C:27]([O:33][CH2:34][CH:35]4[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]4)[C:28]([O:31][CH3:32])=[CH:29][C:30]=3[C:21]([C:18]3[CH:17]=[CH:16][C:15]([OH:14])=[CH:20][CH:19]=3)=[N:22][C:23]=2[NH:44][N:43]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178486399HCID 178486399, compound

Product 1

HCID 178486395HCID 178486395, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1,1-Dimethylethyl 4-{1-methyl-7-(methyloxy)-8-{[(1-methylpiperidin-4-yl)methyl]oxy}-3H-pyrazolo[3,4-c]isoquinolin-5-yl}phenyl carbonate trifluoroacetate (32 mg, 0.049 mmol) was taken into 4 N HCl in dioxane and the mixture was stirred for 1 h at rt. The reaction mixture was concentrated in vacuo. The resulting residue was dissolved in water, frozen, and lyophilized. 4-(1-methyl-7-(methyloxy)-8-{[(1-methylpiperidin-4-yl)methyl]oxy}-3H-pyrazolo[3,4-c]isoquinolin-5-yl)phenol hydrochloride was isolated as a solid (13.0 mg, 0.028 mmol, 57% yield). 1H NMR (400 MHz, DMSO-d6): δ9.71 (br m, 2H), 7.59 (d, 2H), 7.54 (d, 2H), 6.94 (m, 2H), 4.18 (d, 2H), 3.76 (s, 3H), 3.04-2.96 (m, 2H), 2.81 (s, 3H), 2.82-2.74 (m, 2H), 2.15 (m, 1H), 2.04 (br d, 2H), 1.67-1.61 (m, 2H); MS (EI) for C25H28N4O3: 433 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in water
  3. temperaturefrozen

Sources & evidence

ORD record
ord-bd0ef0d835d14f57897415be0ab940f0
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

Loading…