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

HRID 1750544Notes

Reaction equation

HRID 1750544 reaction equation
[CH2:1]([C:3]1[C:4]([NH:13][C@H:14]2[CH2:18][CH2:17][CH2:16][C@@H:15]2[NH:19]C(=O)OC(C)(C)C)=[N:5][CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[N:8]=1)[CH3:2].[ClH:27]>O1CCOCC1>[ClH:27].[CH2:1]([C:3]1[C:4]([NH:13][C@H:14]2[CH2:18][CH2:17][CH2:16][C@@H:15]2[NH2:19])=[N:5][CH:6]=[C:7]([C:9]([F:12])([F:10])[F:11])[N:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118308096tert-butyl ((1S,2S)-2-((3-ethyl-5-(trifluoromethyl)pyrazin-2-yl)amino)cyclopentyl)carbamate

Product 1

HCID 118308132(1S,2S)-1-N-[3-Ethyl-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-ethyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]carbamate (366 mg, 0.98 mmol) in 1,4-dioxane (3 ml) was added HCl in 1,4-dioxane (4M, 3 ml, 12.0 mmol). The reaction was stirred at room temperature for 18 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-0f9cc1e92ba640d19105fd11d9b603de
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

Loading…