Hydrochloric Acid → HCID 118049750, compound

HRID 595860Notes

Reaction equation

HRID 595860 reaction equation
C([N:8](C(OC(C)(C)C)=O)[C:9]1[CH:14]=[N:13][C:12]([C@@H:15]2[CH2:20][CH2:19][CH2:18][C@H:17]([O:21][CH3:22])[CH2:16]2)=[CH:11][N:10]=1)(OC(C)(C)C)=O.Cl>C(Cl)Cl>[CH3:22][O:21][C@H:17]1[CH2:18][CH2:19][CH2:20][C@@H:15]([C:12]2[N:13]=[CH:14][C:9]([NH2:8])=[N:10][CH:11]=2)[CH2:16]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118049792HCID 118049792, compound

Product 1

HCID 118049750HCID 118049750, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(+/−)-N,N-di-Boc-5-((1R,3S)-3-methoxycyclohexyl)pyrazin-2-amine (184 mg, 0.452 mmol) in DCM (4. 515 mL) was added HCl (4M in dioxane) (4.515 mL, 18.06 mmol). The reaction mixture was stirred at room temperature overnight. After the volatile material was removed in vacuo, the residue was dissolved in EtOAc. The organic layer was washed by NaHCO3 solution, water and brine, dried over anhydrous Na2SO4, and concentrated affording (+/−)-5-((1R,3S)-3-methoxycyclohexyl)pyrazin-2-amine in quantitative yield. LCMS (m/z): 208 (MH+), 0.43 min. To a solution of (+/−)-5-((1R,3S)-3-methoxycyclohexyl)pyrazin-2-amine (54 mg, 0.261 mmol) in acetonitrile (4. 008 μL) was added NBS (48.7 mg, 0.274 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 15 min. After quenched with NaHCO3, extracted with EtOAc three times. The organic layer was washed by water and brine, dried over anhydrous Na2SO4, and concentrated to afford 75 mg of (+/−)-3-bromo-5-((1R,3S)-3-methoxycyclohexyl)pyrazin-2-amine in quantitative yield. LCMS (m/z): 286 (MH+), 0.73 min.

Workup

  1. customAfter the volatile material was removed in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThe organic layer was washed by NaHCO3 solution, water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4df140ca6d49493ab8aa038ab4068a99
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

Loading…