Hydrochloric Acid → 1-((3R,4R)-4-methylpiperidin-3-yl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine hydrochloride

HRID 1969776Notes

Reaction equation

[C:1]1([C@@H:13]2[C@H:18]([CH3:19])[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]2)[N:5]2[C:6]3[CH:12]=[CH:11][NH:10][C:7]=3[N:8]=[CH:9][C:4]2=[CH:3][N:2]=1.[ClH:27]>O1CCOCC1>[ClH:27].[CH3:19][C@@H:18]1[CH2:17][CH2:16][NH:15][CH2:14][C@@H:13]1[C:1]1[N:5]2[C:6]3[CH:12]=[CH:11][NH:10][C:7]=3[N:8]=[CH:9][C:4]2=[CH:3][N:2]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (3R,4R)-tert-butyl 3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)-4-methyl-piperidine-1-carboxylate (27.9 g, 78 mmol) in 1,4-dioxane (400 mL) was added HCl (4 N in 1,4-dioxane, 58.9 mL, 235 mmol). The resulting suspension was heated at about 60° C. for about 1 h. The reaction was allowed to cool to ambient temperature and then was filtered, washed with 1,4-dioxane (100 mL) followed by Et2O (100 mL), to give 1-((3R,4R)-4-methylpiperidin-3-yl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine hydrochloride (20.6 g, 89%) as a tan solid: LC/MS (Table 1, Method b) Rt=1.27 min; MS m/z: 256 (M+H)+.

Workup

temperatureto cool to ambient temperature
filtrationwas filtered
washwashed with 1,4-dioxane (100 mL)

Sources & evidence

ORD record: ord-b531253da523483f825f17560bfe1a28
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426411B2

Reaction notes

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