Methanol → HCID 70664661, compound

HRID 1403551Notes

Reaction equation

HRID 1403551 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:36])[C:15]2[C:16]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)=[N:17][C:18]3[C:23]([N:24]=2)=[CH:22][C:21]([C:25]([O:27][CH3:28])=[O:26])=[CH:20][CH:19]=3)[CH2:10][CH2:9]1)=O)(C)(C)C.CO>Cl>[F:35][C:32]1[CH:33]=[CH:34][C:29]([C:16]2[C:15]([N:14]([CH3:36])[CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[N:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:25]([O:27][CH3:28])=[O:26])[CH:22]=3)[N:17]=2)=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 70665039HCID 70665039, compound

Product 1

HCID 70664661HCID 70664661, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The solution of methyl 3-((1-(tert-butoxycarbonyl)piperidin-4-yl)(methyl)amino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate (210 mg, crude) in hydrogen chloride(g)/MeOH (50 mL) was stirred overnight at room temperature and then concentrated in vacuo. The residue was dissolved in water (50 mL) and adjusted to pH 8 with sodium bicarbonate, extracted with dichloromethane (5×30 mL), dried over anhydrous magnesium sulfate and concentrated in vacuo. The product was precipitated by the addition ether (20 mL) to afford methyl 2-(4-fluorophenyl)-3-(methyl(piperidin-4-yl)amino)quinoxaline-6-carboxylate as a yellow solid (100 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water (50 mL)
  3. extractionextracted with dichloromethane (5×30 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe product was precipitated by the addition ether (20 mL)

Sources & evidence

ORD record
ord-7846fea7a27f45d4a255a741c88fecce
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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