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

HRID 2204589Notes

Reaction equation

[S:1]([N:11]1[C:15]2[N:16]=[CH:17][C:18]3[N:19]([C:20]([C@@H:23]4[CH2:27][CH2:26][C@H:25]([NH:28]C(=O)OC(C)(C)C)[CH2:24]4)=[N:21][N:22]=3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[ClH:36]>O1CCOCC1>[ClH:36].[S:1]([N:11]1[C:15]2[N:16]=[CH:17][C:18]3[N:19]([C:20]([C@@H:23]4[CH2:27][CH2:26][C@H:25]([NH2:28])[CH2:24]4)=[N:21][N:22]=3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of tert-butyl (1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentylcarbamate (8.22 g, 16.6 mmol) in 1,4-dioxane (32 mL) was added HCl (4 N in 1,4-dioxane, 16.6 mL, 66.2 mmol), and the reaction mixture was heated at about 60° C. for about 1.5 h then stirred at ambient temperature overnight. The reaction mixture was filtered, while rinsing with Et2O (100 mL). The filter cake was dried under vacuum to give a light brown solid that was further dried in a vacuum oven at about 50° C. to give (1S,3R)-3-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanamine hydrochloride (7.61 g, 93%) as a beige solid: LC/MS (Table 2, Method d) Rt=1.09 min; MS m/z: 397 (M+H)+.

Workup

filtrationThe reaction mixture was filtered
washwhile rinsing with Et2O (100 mL)
customThe filter cake was dried under vacuum
customto give a light brown solid that
customwas further dried in a vacuum oven at about 50° C.

Sources & evidence

ORD record: ord-dbfb79a8804444a8afaf806b18419394
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365579B2

Reaction notes

Loading…