Hydrochloric Acid → HCID 58382051, compound

HRID 1628066Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:10]3=[N:11][CH:12]=[C:13]([NH:15][NH:16]C(OC(C)(C)C)=O)[N:14]=[C:9]3[CH:8]=2)[CH:4]=[N:3]1.Cl.O1CCOCC1>CCOC(C)=O>[NH:15]([C:13]1[N:14]=[C:9]2[CH:8]=[C:7]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)[N:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:10]2=[N:11][CH:12]=1)[NH2:16]

Participants

Conditions

Temperature: 60 °C

Procedure

To a flask was added tert-butyl 2-(6-(1-methyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarboxylate (0.152 g, 0.331 mmol, Preparation #O.1), HCl (4.0 M in 1,4-dioxane, 0.827 mL, 3.31 mmol) and 1,4-dioxane (5 mL). The mixture was heated to about 60° C. for about 1 h then stirred at rt overnight. The mixture was diluted with EtOAc (10 mL), washed with aqueous saturated NaHCO3, dried over anhydrous MgSO4 and concentrated in vacuo to give 2-hydrazinyl-6-(1-methyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine (0.100 g, 84%): LC/MS (Table 2, Method c) Rt=1.43 min; MS m/z 360 (M+H)+.

Workup

washwashed with aqueous saturated NaHCO3
dry with materialdried over anhydrous MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-6490b807feda4731867def4c851cbdbb
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785639B2

Reaction notes

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