Hydrochloric Acid → 8-Bromo-2-(1-piperidin-4-yl-1H-pyrazol-4-yl)-quinoxaline

HRID 216736Notes

Reaction equation

HRID 216736 reaction equation
Cl.CCO.C(OC([N:12]1[CH2:17][CH2:16][CH:15]([N:18]2[CH:22]=[C:21]([C:23]3[CH:32]=[N:31][C:30]4[C:25](=[C:26]([Br:33])[CH:27]=[CH:28][CH:29]=4)[N:24]=3)[CH:20]=[N:19]2)[CH2:14][CH2:13]1)=O)(C)(C)C>>[Br:33][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]2[C:25]=1[N:24]=[C:23]([C:21]1[CH:20]=[N:19][N:18]([CH:15]3[CH2:16][CH2:17][NH:12][CH2:13][CH2:14]3)[CH:22]=1)[CH:32]=[N:31]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 59392739HCID 59392739, compound

Product 1

HCID 593926308-Bromo-2-(1-piperidin-4-yl-1H-pyrazol-4-yl)-quinoxaline

Conditions

Temperature
50 °C

Procedure

A 1.2 M solution of HCl in EtOH (60 ml, 72 mmol) is added to 4-[4-(8-Bromo-quinoxalin-2-yl)-pyrazol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (Step 94.1, 1.98 g, 4.32 mmol) and the reaction mixture is heated at 50° C. for 12 h. After cooling, the yellow suspension is concentrated under vacuo and the residue is diluted with CH2Cl2, poured onto a saturated solution of NaHCO3 and extracted 3× with CH2Cl2. The combined organic layers are washed with water, brine, dried over Na2SO4, filtered and the filtrate is concentrated in vacuo. The residue is used without further purification in the next step, and afford the title compound as pale orange solid, Rt=0.802 min (Acquity HPLC BEH C18, 2.1×50 mm, 1.7 micron, detection 215 nM, 0.1 min 2% CH3CN in H2O, 2% to 100% CH3CN in H2O in 1.5 min, 0.4 min 100% CH3CN+0.1% TFA, flow rate 1.0 ml/min); MS: 358 (M+1, 79Br)+

Workup

  1. temperatureAfter cooling
  2. concentrationthe yellow suspension is concentrated under vacuo
  3. additionthe residue is diluted with CH2Cl2
  4. additionpoured onto a saturated solution of NaHCO3
  5. extractionextracted 3× with CH2Cl2
  6. washThe combined organic layers are washed with water, brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationthe filtrate is concentrated in vacuo
  10. customThe residue is used without further purification in the next step

Sources & evidence

ORD record
ord-9c88ca5c96ed49b9ad4b2bd0b5154ca5
Source dataset
uspto-grants-2012_06
Patent number
US08193189B2

Reaction notes

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