Sodium Bicarbonate → 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)cyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one

HRID 40004

Reaction equation

HRID 40004 reaction equation
O[C:2]1([CH2:9][CH2:10][N:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=3)N=[CH:13][C:12]2=[O:23])[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[O:24]1[C:33]2[CH:32]=[C:31]([CH2:34][NH2:35])N=[CH:29][C:28]=2[O:27][CH2:26][CH2:25]1.[C:36](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:37].[Na+].[C:50](=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.ClCCl>[O:27]1[C:28]2[CH:29]=[CH:50][C:31]([CH2:34][NH:35][CH:5]3[CH2:4][CH2:3][CH:2]([CH2:9][CH2:10][N:11]4[C:20]5[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=5)[C:36]([CH3:37])=[CH:13][C:12]4=[O:23])[CH2:7][CH2:6]3)=[CH:32][C:33]=2[O:24][CH2:25][CH2:26]1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 593979991-(2-(1-hydroxy-4-oxocyclohexyl)ethyl)-7-methoxyquinoxalin-2(1H)-oneHCID 593981871-(2,3-Dihydro[1,4]dioxino[2,3-c]pyridin-7-yl)methanamine

Product 1

HCID 593984071-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)cyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

To 4 mL of a dichloromethane solution containing 90 mg of 1-(2-(1-hydroxy-4-oxocyclohexyl)ethyl)-7-methoxyquinoxalin-2(1H)-one, 2 mL of a dichloromethane solution containing 57 mg of 1-(2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-yl)methaneamine and 24 μL of acetic acid were added at room temperature, and stirred at the same temperature for 1.5 hours. To the reaction mixture, 59 mg of sodium triacetoxyborohydride was added, and stirred at room temperature for 1.5 hours. To the reaction mixture, aqueous saturated sodium hydrogen carbonate solution and chloroform were added. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by basic silica gel column chromatography [eluent; chloroform:methanol=50:1], to give (A) 29 mg as a light red oil and (B)24 mg as a light red oil. To the purified products A and B, a mixture of diethyl ether and hexane was added, respectively, and each resulting solid was filtered to give (A) 28 mg of 1-(2-(4-((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)-1-hydroxycyclohexyl)ethyl)-7-methoxyquinoxalin-2(1H)-one as a light red solid and (B) 21 mg of 1-(2-(4-((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)-1-hydroxycyclohexyl)ethyl)-7-methoxyquinoxalin-2(1H)-one as a light red solid.

Workup

  1. additionwere added at room temperature
  2. stirringstirred at room temperature for 1.5 hours
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with chloroform
  5. washwashed with aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by basic silica gel column chromatography [eluent; chloroform:methanol=50:1]

Sources & evidence

ORD record
ord-19a3a24807dd49969a171285d5e2fef2
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Linked notes

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