Hydrochloric Acid → HCID 89782041, compound

HRID 1056222Notes

Reaction equation

HRID 1056222 reaction equation
[C:1]([NH:5][C:6]1[C:7](F)=[N:8][C:9]2[C:14]([N:15]=1)=[C:13]([C:16](=[O:18])[CH3:17])[CH:12]=[CH:11][CH:10]=2)([CH3:4])([CH3:3])[CH3:2].O1CCOCC1.[ClH:26]>>[C:1]([NH:5][C:6]1[C:7]([Cl:26])=[N:8][C:9]2[C:14]([N:15]=1)=[C:13]([C:16](=[O:18])[CH3:17])[CH:12]=[CH:11][CH:10]=2)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 89782158HCID 89782158, compound

Product 1

HCID 89782041HCID 89782041, compoundYield 89%

Procedure

A mixture of 1-(3-(tert-butylamino)-2-fluoroquinoxalin-5-yl)ethanone (343b) (300 mg, 1.14 mmol) in 4 M HCl in dioxane (2.87 mL, 11.48 mmol) was stirred at RT for 16 h under a drying tube. Lcms indicated the reaction was not completed. The reaction mixture was heated at 70° C. for 1.5 h. The reaction was quenched with saturated aq. NaHCO3 (200 mL), diluted with DCM (100 mL), added to a separatory funnel, and extracted with DCM (3×100 mL) before the organic layer was separated, dried over Na2SO4, and concentrated to give 1-(3-(tert-butylamino)-2-chloroquinoxalin-5-yl)ethanone (345a, 285 mg, 1.02 mmol, 89% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.57 (s, 9H) 2.86 (s, 3H) 5.73 (br. s., 1H) 7.39 (t, J=8.02 Hz, 1H) 7.83 (dd, J=7.43, 1.56 Hz, 1H) 7.89 (dd, J=8.22, 1.57 Hz, 1H). MS (ESI, pos. ion) m/z: 278.2 (M+1).

Workup

  1. temperatureThe reaction mixture was heated at 70° C. for 1.5 h
  2. customThe reaction was quenched with saturated aq. NaHCO3 (200 mL)
  3. additiondiluted with DCM (100 mL)
  4. additionadded to a separatory funnel
  5. extractionextracted with DCM (3×100 mL) before the organic layer
  6. customwas separated
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f1ec0eb8bce44aedad306c085524e14a
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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