Acetonitrile → HCID 131736043, compound

HRID 1049741Notes

Reaction equation

I[C:2]1[CH:33]=[CH:32][CH:31]=[CH:30][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:19](=[O:20])[CH2:18][C:17](=[O:21])[NH:16][C:15]3[C:22]4[C:27]([CH:28]=[CH:29][C:14]2=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:9][CH:8]=1)=[O:5].[CH2:34]([Sn](CCCC)(CCCC)CCCC)[CH:35]=[CH2:36].C(#N)C>C1(C)C=CC=CC=1>[CH:34]([C:2]1[CH:33]=[CH:32][CH:31]=[CH:30][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:19](=[O:20])[CH2:18][C:17](=[O:21])[NH:16][C:15]3[C:22]4[C:27]([CH:28]=[CH:29][C:14]2=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:9][CH:8]=1)=[O:5])=[CH:35][CH3:36]

Participants

Conditions

Temperature: 110 °C

Procedure

5-[4-(2-Iodobenzoylamino)phenyl]-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dione (70 mg, 0.128 mmol), allyltributyltin (98 mg, 0.32 mmol), and tetrakistriphenylphosphine palladium(0) (15 mg, 12.8 μmol) were dissolved in anhydrous toluene (0.6 mL), and the solution was stirred at 110° C. for 16 hours. The reaction mixture was left to cool, and then added with acetonitrile, the mixture was washed with petroleum ether, and the solvent of the acetonitrile layer was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/1) to obtain the title compound (40 mg, yield 68%).

Workup

waitThe reaction mixture was left
temperatureto cool
washthe mixture was washed with petroleum ether
customthe solvent of the acetonitrile layer was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/1)

Sources & evidence

ORD record: ord-0c29225adc2e4596903ac1804c5716ce
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382236B2

Reaction notes

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