Tetrahydrofuran → HCID 90411794, compound

HRID 2175958Notes

Reaction equation

HRID 2175958 reaction equation
[CH3:1][C:2]([O-])([CH3:4])C.[Na+].Cl[C:8]1[CH:17]=[N:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.[NH4+:18].[Cl-].C([O-])([O-])=O.[Na+].[Na+].[CH2:26]1[CH2:30][O:29][CH2:28][CH2:27]1>>[CH:4]12[NH:18][CH:28]([CH2:1][CH2:2]1)[CH2:27][CH:26]2[CH2:30][O:29][C:8]1[CH:17]=[N:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 2389382-ChloroquinoxalineHCID 23676156Sodium t-butoxide

Product 1

HCID 90411794HCID 90411794, compoundYield 78%

Procedure

To intermediate B-10 (240 mg, 1.1 mmol) in THF (4 mL) was added NaOtBu (130 mg, 1.4 mmol). The reaction was heated at reflux for 15 min and 2-chloroquinoxaline (207 mg, 1.3 mmol) was added. After 45 min, the reaction was cooled to rt and ½ saturated NH4Cl (aq) was added. The solution was made slightly basic with 5% Na2CO3 (aq) and extracted with DCM (3×). The combined organics were dried (Na2SO4). The resulting compound was treated with TFA in DCM. After the reaction was complete, the reaction was concentrated, neutralized with 5% Na2CO3 and extracted with DCM. The combined organics were dried (Na2SO4). Purification via silica gel chromatography (1-7% (2M NH3 in MeOH)/DCM) gave the title compound (208 mg, 78%). MS (ESI) mass calcd. for C15H17N3O, 255.1; m/z found 256.2 [M+H]+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 15 min
  3. additionwas added
  4. extractionextracted with DCM (3×)
  5. dry with materialThe combined organics were dried (Na2SO4)
  6. additionThe resulting compound was treated with TFA in DCM
  7. concentrationthe reaction was concentrated
  8. extractionextracted with DCM
  9. dry with materialThe combined organics were dried (Na2SO4)
  10. customPurification via silica gel chromatography (1-7% (2M NH3 in MeOH)/DCM)

Sources & evidence

ORD record
ord-0eb03018e1764d43ae99c5843f2865f1
Source dataset
uspto-grants-2015_06
Patent number
US09062078B2

Reaction notes

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