Dimethyl Sulfoxide → Methyl 3-(3,3-dimethylpiperidin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylate

HRID 717033노트

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HRID 717033 반응식
Cl[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2.[CH3:23][C:24]1([CH3:30])[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]1.CS(C)=O>O>[CH3:23][C:24]1([CH3:30])[CH2:29][CH2:28][CH2:27][N:26]([C:2]2[C:3]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[N:4][C:5]3[C:10]([N:11]=2)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=3)[CH2:25]1

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 709423,3-DimethylpiperidineHCID 77231184Methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate

생성물 1

HCID 67041999Methyl 3-(3,3-dimethylpiperidin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylate

시약·촉매·용매 1

HCID 962Water용매

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온도
100 °C

실험 절차

Into a 10-mL sealed tube, was placed methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate (150 mg, 0.47 mmol, 1.00 equiv), 3,3-dimethylpiperidine (107 mg, 0.95 mmol, 2.00 equiv), DMSO (2 mL). The resulting solution was stirred overnight at 100° C. in an oil bath. The resulting solution was diluted with 20 mL of H2O. The resulting solids were collected by filtration. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:40). This resulted in 120 mg (64%) of methyl 3-(3,3-dimethylpiperidin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylate as a yellow solid.

후처리

  1. customInto a 10-mL sealed tube
  2. filtrationThe resulting solids were collected by filtration
  3. customThe residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:40)
  4. customThis resulted in 120 mg (64%) of methyl 3-(3,3-dimethylpiperidin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylate as a yellow solid

출처 및 근거

ORD 기록
ord-22ebf4b44c6a403ea3f723d7607272d9
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193693B2

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