Sodium Iodide → 2-[4-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)butyl]-1H-isoindole-1,3(2H)-dione

HRID 1984437

Reaction equation

[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[I-].[Na+].Cl[CH2:16][CH2:17][CH2:18][CH2:19][C:20]1[N:21]([CH2:34][CH2:35][CH3:36])[N:22]=[C:23]2[C:32]=1[C:31]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:25]=[C:24]2[NH2:33]>CN(C=O)C>[NH2:33][C:24]1[C:23]2=[N:22][N:21]([CH2:34][CH2:35][CH3:36])[C:20]([CH2:19][CH2:18][CH2:17][CH2:16][N:5]3[C:1](=[O:11])[C:2]4[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:4]3=[O:6])=[C:32]2[C:31]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[N:25]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of potassium phthalimide (6.61 g, 35.7 mmol), sodium iodide (0.669 g, 4.46 mmol) and 1-(4-chlorobutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine (prepared as described in Example 46, 5.65 g, 17.8 mmol) in DMF (30 mL) was heated at 90° C. for 3 hours. The reaction mixture was allowed to cool to room temperature overnight, then was diluted with ice water (300 mL) and stirred for 10 minutes. A solid formed that was collected by filtration and dried to yield 7.14 g of 2-[4-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)butyl]-1H-isoindole-1,3 (2H)-dione as a tan solid, mp 204-206° C. 1H-NMR (300 MHz, CDCl3) δ 7.86-7.70 (m, 5H), 7.69-7.64 (m, 1H), 7.43-7.36 (m, 1H), 7.29-7.22 (m, 1H), 5.37 (br s, 2H), 4.30 (t, J=7.3 Hz, 2H), 3.77 (t, J=6.8 Hz, 2H), 3.31-3.21 (m, 2H), 2.05-1.75 (m, 6H), 0.98 (t, J=7.4 Hz, 3H).

Workup

temperatureto cool to room temperature overnight
customA solid formed that
filtrationwas collected by filtration
customdried

Sources & evidence

ORD record: ord-c02c5b1a53f040749238196d523d01f7
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544697B2

Linked notes

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