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

HRID 1750529Notes

Reaction equation

HRID 1750529 reaction equation
[CH3:1][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.[ClH:26]>O1CCOCC1>[ClH:26].[CH3:1][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:9])([F:10])[F:11])[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118308071tert-Butyl N-[(1S,2S)-2-{[3-methyl-5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]carbamate

Product 1

HCID 118308266(1S,2S)-1-N-[3-Methyl-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-methyl-5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]carbamate (580 mg, 1.614 mmol) in 1,4-dioxane (5 ml) was added HCl in 1,4-dioxane (4M, 4 ml, 16.00 mmol). The reaction was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and azeotropically distilled with toluene to afford the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. distillationazeotropically distilled with toluene

Sources & evidence

ORD record
ord-c2d6fa1b46ac43dea7e7eeb88abc0e19
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

Loading…