2-(6,7-Dimethoxy-quinoxalin-2-yl)-2-aza-bicyclo[2.2.2]octan-3-one → HCID 178486819, compound

HRID 567741

Reaction equation

HRID 567741 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([N:15]1C(=O)[CH:19]3[CH2:22][CH2:23][CH:16]1[CH2:17][CH2:18]3)[CH:7]=[N:6]2.[CH3:24][O-:25].[Na+].[CH3:27][OH:28]>CO>[CH3:24][O:25][C:27]([C@H:19]1[CH2:18][CH2:17][C@H:16]([NH:15][C:8]2[CH:7]=[N:6][C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=2)[CH2:23][CH2:22]1)=[O:28]

Participants

4

Reactant 2

HCID 225731612-(6,7-Dimethoxy-quinoxalin-2-yl)-2-aza-bicyclo[2.2.2]octan-3-oneHCID 23694274Sodium methanolate methanol

Product 1

HCID 178486819HCID 178486819, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(6,7-dimethoxy-quinoxalin-2-yl)-2-aza-bicyclo[2.2.2]octan-3-one (100 mg, 0.32 mmole) in 10 mL of methanol is added a freshly prepared NaOMe/methanol solution (54 mg, 1 mmole) and the mixture is stirred at ROOM TEMPERATURE for 0.5 hour before concentrated. Methylene chloride is used to extract and then dried with magnesium sulfate. The residue after filtration and concentration is chromatographed on silica gel (40% ethyl acetate) to give 85 mg (77%) of cis/trans-4-(6,7-dimethoxy-quinoxalin-2-ylamino)-cyclohexanecarboxylic acid methyl ester as a light yellow solid (m.p. 68-80° C.).

Workup

  1. concentrationbefore concentrated
  2. extractionto extract
  3. dry with materialdried with magnesium sulfate
  4. filtrationThe residue after filtration and concentration
  5. customis chromatographed on silica gel (40% ethyl acetate)

Sources & evidence

ORD record
ord-ffc2370ea3d14ff3891a234d8a9eb68d
Source dataset
uspto-grants-2001_01
Patent number
US06180632B2

Linked notes

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