4-Hydroxybenzaldehyde → 4-(1-methyl-8,9-bis{[2-(methyloxy)ethyl]-oxy}-3H-pyrazolo[3,4-c]isoquinolin-5-yl)phenol

HRID 253244

Reaction equation

HRID 253244 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][O:15][CH3:16])=[CH:10][CH:9]=[CH:8][C:7]=1[C:17]1[C:18]([CH3:23])=[N:19][NH:20][C:21]=1[NH2:22].[OH:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1>C(O)(C(F)(F)F)=O>[CH3:23][C:18]1[C:17]2[C:7]3[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[C:11]([O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:10]=[CH:9][C:8]=3[C:29]([C:28]3[CH:31]=[CH:32][C:25]([OH:24])=[CH:26][CH:27]=3)=[N:22][C:21]=2[NH:20][N:19]=1

Participants

4

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 178496121HCID 178496121, compound

Product 1

HCID 1784960944-(1-methyl-8,9-bis{[2-(methyloxy)ethyl]-oxy}-3H-pyrazolo[3,4-c]isoquinolin-5-yl)phenolYield 38%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-(2,3-bis{[2-(methyloxy)ethyl]oxy}phenyl)-3-methyl-1H-pyrazol-5-amine (70 mg, 0.22 mmol), and 4-hydroxybenzaldehyde (40 mg, 0.33 mmol) in TFA (2 mL) was stirred in a sealed pressure vessel at 90° C. for 14 h. The reaction mixture was concentrated and purified by HPLC to give 4-(1-methyl-8,9-bis{[2-(methyloxy)ethyl]-oxy}-3H-pyrazolo[3,4-c]isoquinolin-5-yl)phenol (35 mg, 38% yield) as a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ9.90 (br. s, 1H), 7.79 (d, 1H), 7.46 (m, 2H), 7.38 (d, 1H), 6.93 (m, 2H), 4.32 (m, 2H), 4.27 (m, 2H), 3.76 (m, 2H), 3.69 (m, 2H), 3.34 (s, 3H), 3.23 (s, 3H), 2.82 (s, 3H); MS (EI) for C23H25N3O5: 424 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-bbc9d6a4ee3e448fa576024f2d0bdbb9
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Linked notes

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