Hydrochloric Acid → 3-(6-Hydroxymethyl-2-methyl-imidazo[1,2-a]pyrazin-3-yl)-4-(1H-indol-3-yl)-pyrrole-2,5-dione

HRID 216659Notes

Reaction equation

Cl.C([SiH2][O:7][C:8](C1C=CC=CC=1)(C1C=CC=CC=1)[C:9]1[N:10]=[CH:11][C:12]2[N:13]([C:15]([C:19]3[C:20](=[O:34])[NH:21][C:22](=[O:33])[C:23]=3[C:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[NH:26][CH:25]=3)=[C:16]([CH3:18])[N:17]=2)[CH:14]=1)(C)(C)C>O1CCOCC1>[OH:7][CH2:8][C:9]1[N:10]=[CH:11][C:12]2[N:13]([C:15]([C:19]3[C:20](=[O:34])[NH:21][C:22](=[O:33])[C:23]=3[C:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[NH:26][CH:25]=3)=[C:16]([CH3:18])[N:17]=2)[CH:14]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Hydrochloric acid (1.0 ml of a 4.0 M solution in dioxane) is added to 3-[6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-imidazo[1,2-a]pyrazin-3-yl]-4-(1H-indol-3-yl)-pyrrole-2,5-dione (60 mg, 0.098 mmol). The reaction mixture is heated to 50° C. for 16 hours under an atmosphere of argon. After cooling, volatiles are removed in vacuo, and the residue is purified by flash chromatography (gradient of CH2Cl2/MeOH 100:0 to 90:10) to afford the title compound (25 mg, 68%). MS (ES+): 374 (M+H)+.

Workup

temperatureAfter cooling
customvolatiles are removed in vacuo
customthe residue is purified by flash chromatography (gradient of CH2Cl2/MeOH 100:0 to 90:10)

Sources & evidence

ORD record: ord-a9a3ff91b0f0401e8d7a735103104bb3
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193236B2

Reaction notes

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