Hydrochloric Acid → (1S,2S)-1-N-[3-Cyclopropyl-5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride

HRID 1750568Notes

Reaction equation

HRID 1750568 reaction equation
[CH:1]1([C:4]2[C:5]([NH:14][C@H:15]3[CH2:19][CH2:18][CH2:17][C@@H:16]3[NH:20]C(=O)OC(C)(C)C)=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[N:9]=2)[CH2:3][CH2:2]1.[ClH:28]>O1CCOCC1>[ClH:28].[CH:1]1([C:4]2[C:5]([NH:14][C@H:15]3[CH2:19][CH2:18][CH2:17][C@@H:16]3[NH2:20])=[N:6][CH:7]=[C:8]([C:10]([F:12])([F:13])[F:11])[N:9]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118308262tert-Butyl N-[(1S,2S)-2-{[3-cyclopropyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]carbamate

Product 1

HCID 118308108(1S,2S)-1-N-[3-Cyclopropyl-5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl N-[(1S,2S)-2-{[3-cyclopropyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]carbamate (1.54 g, 3.99 mmol) in 1,4-dioxane (14 ml) was added HCl in 1,4-dioxane (4M, 10 ml, 40 mmol). The reaction was stirred at room temperature for 20 hours and was then concentrated in vacuo and azeotropically distilled with toluene to afford the title compound.

Workup

  1. concentrationwas then concentrated in vacuo
  2. distillationazeotropically distilled with toluene

Sources & evidence

ORD record
ord-de352cbc89984acdbab37a740644e4fd
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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