Potassium Carbonate → HCID 59398343, compound

HRID 40015Notes

Reaction equation

HRID 40015 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][C:11]2=[O:22])[CH2:4][CH2:3]1.Br[CH2:24][C:25]1[N:30]=[C:29]2[O:31][CH2:32][CH2:33][O:34][C:28]2=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:34]1[C:28]2[C:29](=[N:30][C:25]([CH2:24][NH:1][CH:2]3[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][N:10]4[C:19]5[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=5)[N:13]=[CH:12][C:11]4=[O:22])[CH2:6][CH2:7]3)=[CH:26][CH:27]=2)[O:31][CH2:32][CH2:33]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 184545116-(Bromomethyl)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridineHCID 593978381-[2-(4-Aminopiperidin-1-yl)ethyl]-7-methoxyquinoxalin-2(1H)-one

Product 1

HCID 59398343HCID 59398343, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 5 mL of an N,N-dimethylformamide solution containing 170 mg of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxyquinoxalin-2(1H)-one and 130 mg of 6-bromomethyl-2,3-dihydro-1,4-dioxino[2,3-b]pyridine, 230 mg of potassium carbonate was added, and stirred at room temperature for 3 days. The solvent was removed under reduced pressure, and the residue thus obtained was purified by silica gel column chromatography [Silica Gel; Kanto Chemical Co., Inc., Silica Gel N, eluent; chloroform:methanol=5:1] to give 95.1 mg of 1-(2-(4-((2,3-dihydro-1,4-dioxino[2,3-b]pyridin-6-yl)methylamino)piperidin-1-yl)ethyl)-7-methoxyquinoxalin-2(1H)-one as a yellow oil.

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure
  3. customthe residue thus obtained
  4. customwas purified by silica gel column chromatography [Silica Gel; Kanto Chemical Co., Inc., Silica Gel N, eluent; chloroform:methanol=5:1]

Sources & evidence

ORD record
ord-efb40509e51543348625484f74a36eef
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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