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

HRID 1750524Notes

Reaction equation

HRID 1750524 reaction equation
[Cl:1][C:2]1[C:3]([NH:12][C@H:13]2[CH2:17][CH2:16][CH2:15][C@@H:14]2[NH:18]C(=O)OC(C)(C)C)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.Cl>O1CCOCC1>[ClH:1].[Cl:1][C:2]1[C:3]([NH:12][C@H:13]2[CH2:17][CH2:16][CH2:15][C@@H:14]2[NH2:18])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118308219tert-Butyl N-[(1S,2S)-2-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]carbamate

Product 1

HCID 118308196(1S,2S)-1-N-[3-Chloro-5-(trifluoromethyl)pyridin-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-chloro-5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]carbamate (2.23 g, 5.87 mmol) in 1,4-dioxane (20 ml) was added HCl in 1,4-dioxane (4 M, 15 ml, 60.0 mmol). The reaction was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo to afford the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-f975cc9d7fef4a45ada75308aef93a44
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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