Hydrochloric Acid → HCID 178420120, compound

HRID 868944Notes

Reaction equation

HRID 868944 reaction equation
CN(C)S([N:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]=[C:7]1[CH2:17][NH:18][C:19]1[CH:28]=[N:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1)(=O)=O.Cl>CO>[C:11]1([C:9]2[N:8]=[C:7]([CH2:17][NH:18][C:19]3[CH:28]=[N:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=3)[NH:6][CH:10]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70117232HCID 70117232, compound

Product 1

HCID 178420120HCID 178420120, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

N,N-Dimethyl-4-phenyl-2-((quinoxalin-2-ylamino)methyl)-1H-imidazole-1-sulfonamide was dissolve in MeOH (5 mL) and 1 M HCl aqueous solution (4.5 mL) was added. The suspension was heated in the microwave (120° C., 40 min) and then poured into a separatory funnel. The phases were separated and the aqueous phase (pH about 2) was washed with Et2O (2×20 mL). The combined organic layers were discarded and the aqueous phase was made basic (pH about 10) by the slow addition of saturated aqueous K2CO3 (10 mL). The basic aqueous phase was extracted with EtOAc (3×40 mL). The combined organic phases were washed with saturated aqueous NaCl (1×50 mL), dried (Na2SO4), filtered and concentrated to give crude N((4-phenyl-1H-imidazol-2-yl)methyl)quinoxalin-2-amine. The material was purified by reverse phase HPLC (Gilson) to give N-((4-phenyl-1H-imidazol-2-yl)methyl)quinoxalin-2-amine as a clear oil. LC-MS m/z 302 (M+H+).

Workup

  1. additionpoured into a separatory funnel
  2. customThe phases were separated
  3. washthe aqueous phase (pH about 2) was washed with Et2O (2×20 mL)
  4. additionby the slow addition of saturated aqueous K2CO3 (10 mL)
  5. extractionThe basic aqueous phase was extracted with EtOAc (3×40 mL)
  6. washThe combined organic phases were washed with saturated aqueous NaCl (1×50 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give crude N((4-phenyl-1H-imidazol-2-yl)methyl)quinoxalin-2-amine
  11. customThe material was purified by reverse phase HPLC (Gilson)

Sources & evidence

ORD record
ord-898d8fb443174e4caf7de3e8e2054db1
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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