Hydrochloric Acid → 2-hydrazinyl-6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine

HRID 1854516Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:30]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[C:16]2=[N:17][CH:18]=[C:19]([NH:21][NH:22]C(OC(C)(C)C)=O)[N:20]=[C:15]2[CH:14]=1.O1CCOCC1.Cl>CCOC(C)=O>[NH:21]([C:19]1[N:20]=[C:15]2[CH:14]=[C:13]([C:6]3[C:5]4[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=4)[N:8]([CH3:12])[CH:7]=3)[N:30]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:36])([CH3:38])[CH3:37])[C:16]2=[N:17][CH:18]=1)[NH2:22]

Participants

Conditions

Temperature: 60 °C

Procedure

To a round bottom flask were added tert-butyl 2-(6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarboxylate (0.272 g, 0.505 mmol) and 1,4-dioxane (5 mL). To the mixture was added HCl (4 N in 1,4-dioxane, 1.26 ml, 5.05 mmol) and the reaction mixture was heated to about 60° C. for about 1 h. The reaction mixture was cooled to room temperature and was diluted with EtOAc (50 mL). The solution was washed with saturated aqueous NaHCO3 (50 mL), dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to give 2-hydrazinyl-6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine (0.19 g, 84%): LC/MS (Table 1, Method d) Rt=1.55 min; MS m/z: 439 (M+H)+.

Workup

temperatureThe reaction mixture was cooled to room temperature
washThe solution was washed with saturated aqueous NaHCO3 (50 mL)
dry with materialdried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-506ac8e972a94b22bd0602c1f05a5152
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962629B2

Reaction notes

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