Iodine → N-(2,6-Diethylphenyl)-8-[(2-iodophenyl)amino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

HRID 81961Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[N:18]=[CH:17][C:16]2[CH2:15][CH2:14][C:13]3[C:19]([C:23]([NH:25][C:26]4[C:31]([CH2:32][CH3:33])=[CH:30][CH:29]=[CH:28][C:27]=4[CH2:34][CH3:35])=[O:24])=[N:20][N:21]([CH3:22])[C:12]=3[C:11]=2[N:10]=1.[Na+].[I-:37].II>O1CCOCC1.ClCCl.CO.[Cu]I>[CH2:34]([C:27]1[CH:28]=[CH:29][CH:30]=[C:31]([CH2:32][CH3:33])[C:26]=1[NH:25][C:23]([C:19]1[C:13]2[CH2:14][CH2:15][C:16]3[CH:17]=[N:18][C:9]([NH:8][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[I:37])=[N:10][C:11]=3[C:12]=2[N:21]([CH3:22])[N:20]=1)=[O:24])[CH3:35]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution 8-[(2-bromophenyl)amino]-N-(2,6-diethylphenyl)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (68 mg, 0.129 mmol) in dioxane (0.5 mL) in a sealed tube, NaI (38 mg, 0.257 mmol), CuI (1.2 mg, 0.006 mmol), iodine (74 mg, 0.129 mmol) and trans-N,N′-dimethylcycloesane-1,2-diammine were added. The mixture was then heated at 150° C. for 12 h. Solvent evaporated to dryness and the crude solid was purified by flash chromatography on silica gel (eluant: dichloromethane/methanol: 8/2/) to 35 mg of the title compound (50% yield).

Workup

customSolvent evaporated to dryness

Sources & evidence

ORD record: ord-d85869a66b8d4bcbbe0f396fc8c3071a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846701B2

Reaction notes

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