Hydrochloric Acid → HCID 118308100, compound

HRID 1750519Notes

Reaction equation

HRID 1750519 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[N:4]=[CH:5][C:6]([NH:9][C@H:10]2[CH2:14][CH2:13][CH2:12][C@@H:11]2[NH:15]C(=O)OC(C)(C)C)=[N:7][CH:8]=1.BrN1C(=O)CCC1=O.[ClH:33].O1CCOCC1>C(Cl)Cl>[ClH:33].[Cl:33][C:5]1[C:6]([NH:9][C@H:10]2[CH2:14][CH2:13][CH2:12][C@@H:11]2[NH2:15])=[N:7][CH:8]=[C:3]([C:2]([F:24])([F:23])[F:1])[N:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67184N-bromobutanimideHCID 118308243HCID 118308243, compound

Product 1

HCID 118308100HCID 118308100, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]carbamate (1.04 g, 3.00 mmol) in dry DCM (10 ml) at 0° C. under an atmosphere of nitrogen was added 1-bromopyrrolidine-2,5-dione (CAS number 128-08-5; 0.80 g, 4.50 mmol). The reaction was allowed to warm to room temperature and stirred for 17 hours and then was concentrated in vacuo. The resulting residue was purified by column chromatography (basic silica, 0-50% ethyl acetate/petrol). To this was then added HCl in 1,4-dioxane (4 M, 7.51 ml, 30.0 mmol) and stirred at room temperature for 72 hours. The reaction mixture was concentrated in vacuo and azeotropically distilled with toluene to afford the title compound.

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe resulting residue was purified by column chromatography (basic silica, 0-50% ethyl acetate/petrol)
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. distillationazeotropically distilled with toluene

Sources & evidence

ORD record
ord-9637bc78655b4303b14f0de3439aada5
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

Loading…