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

HRID 1750500Notes

Reaction equation

HRID 1750500 reaction equation
C[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])[N:7]=1.[ClH:26].O1CCOC[CH2:28]1>CO>[ClH:26].[CH3:28][N:12]([C:3]1[CH:2]=[N:7][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:5][N:4]=1)[C@H:13]1[CH2:17][CH2:16][CH2:15][C@@H:14]1[NH2:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 118308261tert-Butyl N-[(1S,2S)-2-{[3-methyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]carbamate

Product 1

HCID 118308127(1S,2S)-1-N-Methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl N-[(1S,2S)-2-{[3-methyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]carbamate (480 mg, 1.332 mmol) in methanol (5 ml) was added HCl in 1,4-dioxane (4 M, 3.33 ml, 13.32 mmol). The reaction was stirred at room temperature overnight and then concentrated in vacuo, azeotropically distilled with toluene to afford the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. distillationazeotropically distilled with toluene

Sources & evidence

ORD record
ord-e0a6fbbe63ad405995005a973b29e01b
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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