Imidazole → HCID 178433635, compound

HRID 2271108Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:24](=[O:25])[C:11]3=[CH:12][NH:13][C:14]([CH3:23])=[C:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18](I)[CH:17]=4)[C:10]3=[N:9]2)=[CH:4][CH:3]=1.[NH:26]1[CH:30]=[CH:29][N:28]=[CH:27]1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.[Cu]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:24](=[O:25])[C:11]3=[CH:12][NH:13][C:14]([CH3:23])=[C:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([N:26]5[CH:30]=[CH:29][N:28]=[CH:27]5)[CH:17]=4)[C:10]3=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 2-(4-chlorophenyl)-2,5-dihydro-7-(3-iodophenyl)-6-methylpyrazolo[4,3-c]pyridin-3-one (0.100 g, 0.217 mmol), imidazole (33.9 mg, 0.498 mmol), potassium carbonate (29.9 mg, 0.216 mmol), and copper bronze (1 mg) in 1-methyl-2-pyrrolidinone (0.6 ml) was heated at 140° C. under nitrogen for 90 h. Purification by flash chromatography (silica gel, 3-10% MeOH/CH2Cl2) gave 30.3 mg (35%) of the title compound. This was recrystallised from CH2Cl2-MeOH-EtOAc; 1H NMR (400 MHz, DMSO-d6) δ2.29 (3H, s), 7.16 (1H, br s), 7.42 (2H, d), 7.50 (1H, d, J 7.6 Hz), 7.65 (1H, t J 7.8 Hz), 7.73 (1H, d, J 8.1 Hz), 7.80 (1H, s), 7.85 (1H, br s), 8.11 (2H, d), 8.36 (1H, br s), 8.61 (1H, s), 12.53 (1H, br d, J 5.6 Hz); MS (ES+) m/z 402/404 [MH]+.

Workup

customPurification by flash chromatography (silica gel, 3-10% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-5b475528b5e9407c996c5ea72a5cfd8c
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06333336B1

Reaction notes

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