Hydrochloric Acid → (1S,3R)-3-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanamine hydrochloride

HRID 2204530Notes

Reaction equation

[C:1]1([C@@H:13]2[CH2:17][CH2:16][C@H:15]([NH:18]C(=O)OC(C)(C)C)[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=[N:3][N:2]=1.[ClH:26]>O1CCOCC1>[ClH:26].[C:1]1([C@@H:13]2[CH2:17][CH2:16][C@H:15]([NH2:18])[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=[N:3][N:2]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of tert-butyl (1S,3R)-3-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentylcarbamate (1.57 g, 4.59 mmol) in 1,4-dioxane (45 mL) was added HCl (4 M in 1,4-dioxane, 8.0 mL, 32.0 mmol). The reaction mixture was then heated at about 60° C. After about 2 h, the reaction mixture was cooled to ambient temperature, filtered, while washing with Et2O (50 mL) and the solid was dried in a vacuum oven overnight at about 60° C. to give (1S,3R)-3-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanamine hydrochloride (1.38 g, 95%): LC/MS (Table 2, Method a) Rt=0.74 min; MS m/z: 243 (M+H)+.

Workup

temperaturethe reaction mixture was cooled to ambient temperature
filtrationfiltered
washwhile washing with Et2O (50 mL)
customthe solid was dried in a vacuum oven overnight at about 60° C.

Sources & evidence

ORD record: ord-d9f288955c844daea0c2908829a1176e
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365579B2

Reaction notes

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