Hydrochloric Acid → 2-(4-Chloro-2-oxo-1,2-dihydropyridin-3-yl)-4-methyl-6-(1-methylpiperidin-4-yl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione

HRID 69351Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8]C)[C:3]=1[C:10]1[NH:31][C:13]2=[CH:14][C:15]3[C:16](=[O:30])[N:17]([CH:23]4[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]4)[C:18](=[O:22])[C:19]=3[C:20]([CH3:21])=[C:12]2[N:11]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=1[C:10]1[NH:31][C:13]2=[CH:14][C:15]3[C:16](=[O:30])[N:17]([CH:23]4[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH2:28]4)[C:18](=[O:22])[C:19]=3[C:20]([CH3:21])=[C:12]2[N:11]=1

Participants

Conditions

Temperature: 47.5 °C

Procedure

A solution of 2-(4-chloro-2-methoxypyridin-3-yl)-4-methyl-6-(1-methylpiperidin-4-yl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione in a mixture of 1,4-dioxane and concentrated HCl was heated at 45-50° C. for 14 h. After the end of reaction was established by TLC, the reaction mixture was concentrated under vacuum to afford a crude product as a yellow solid, which was used for the next step without further purification. 1H NMR (500 MHz, DMSO-d6) δ 12.60 (s, 1H, NH), 9.90 (s, 1H, NH), 7.90 (s, 1H, ArH), 7.70 (d, J=7.0 Hz, 1H, ArH), 6.58 (d, J=7.5 Hz, 1H, ArH), 4.34-4.29 (m, 1H, CH), 3.53-3.50 (m, 2H, CH2), 3.20-3.13 (m, 2H, CH2), 2.87 (s, 3H, CH3), 2.76 (d, J=4.5 Hz, 3H, CH3), 2.66-2.59 (m, 2H, CH2), 1.96-1.93 (m, 2H, CH2); Mass (ESI, positive) m/z 426.1 [M+H]+.

Workup

customAfter the end of reaction
concentrationthe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record: ord-c21013f5a0c3419eaa33e23c121f2d70
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822500B2

Reaction notes

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