Hydrochloric Acid → HCID 11668799, compound

HRID 2356950Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

230 mg 3-(1-acetyl-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-5,5-dimethyl-1-quinolin-4-ylmethyl-imidazolidine-2,4-dione were dissolved in 5 ml water and 5 ml of an aqueous 2 N solution of hydrochloric acid in a process vial. After sealing with a teflon septum the vial was placed in the microwave cavity and the reaction mixture was stirred for 15 minutes at 120° C. by microwave-assisted heating (Emrys Optimizer, Personal Chemistry). The solvent was removed under reduced pressure and the residue purified by preparative HPLC (C18 reverse phase column, elution with a water/acetonitrile gradient with 0.1% trifluoroacetic acid). Lyophilization of the solution yielded a white solid.

Workup

temperatureby microwave-assisted heating (Emrys Optimizer, Personal Chemistry)
customThe solvent was removed under reduced pressure
customthe residue purified by preparative HPLC (
washC18 reverse phase column, elution with a water/acetonitrile gradient with 0.1% trifluoroacetic acid)
customLyophilization of the solution yielded a white solid

Sources & evidence

ORD record: ord-52b4762130494070b9ad1fc5935bec91
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759379B2

Reaction notes

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