HCID 58382116, compound → HCID 58382292, compound

HRID 1628013Notes

Reaction equation

[Si]([O:8][CH2:9][CH2:10][CH2:11][C:12](=S)[NH:13][CH2:14][C:15]1[N:16]=[C:17]2[CH:23]=[C:22]([C:24]3[C:32]4[C:27](=[CH:28][CH:29]=[C:30]([O:33][CH3:34])[CH:31]=4)[N:26]([CH3:35])[CH:25]=3)[N:21]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])[C:18]2=[N:19][CH:20]=1)(C(C)(C)C)(C)C>FC(F)(F)C(O[Hg]OC(=O)C(F)(F)F)=O.O1CCOCC1>[CH3:34][O:33][C:30]1[CH:31]=[C:32]2[C:27](=[CH:28][CH:29]=1)[N:26]([CH3:35])[CH:25]=[C:24]2[C:22]1[N:21]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])[C:18]2[N:19]=[CH:20][C:15]3[N:16]([C:12]([CH2:11][CH2:10][CH2:9][OH:8])=[N:13][CH:14]=3)[C:17]=2[CH:23]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A flask was charged with 4-(tert-butyldimethylsilyloxy)-N-((6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)butanethioamide (0.158 g, 0.241 mmol) and 1,4-dioxane (3 mL). To the mixture was added bis(2,2,2-trifluoroacetoxy)mercury (0.103 g, 0.241 mmol). The mixture was heated to about 65° C. for 1 h. The mixture was then filtered and concentrated under reduced pressure. The material was purified using silica gel chromatography with an elution gradient of 15 to 100% EtOAc/heptane followed by 0 to 5% MeOH/DCM to give 3-(7-(5-methoxy-1-methyl-1H-indol-3-yl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)propan-1-ol (0.022 g, 18%): LC/MS (Table 2, Method b) Rt=2.59 min; MS m/z 506 (M+H)+.

Workup

filtrationThe mixture was then filtered
concentrationconcentrated under reduced pressure
customThe material was purified

Sources & evidence

ORD record: ord-f545753300c448a9a2e1bb88c1366c8d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785639B2

Reaction notes

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