N-(2,4-dimethoxybenzyl)-1,2,4-thiadiazol-5-amine → 4-chloro-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)quinoline-7-sulfonamide

HRID 1473516노트

반응식

HRID 1473516 반응식
[CH3:1][O:2][C:3]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:4]=1[CH2:5][NH:6][C:7]1[S:11][N:10]=[CH:9][N:8]=1.[Cl:18][C:19]1[C:28]2[C:23](=[CH:24][C:25]([S:29](OC3C(F)=C(F)C(F)=C(F)C=3F)(=[O:31])=[O:30])=[CH:26][CH:27]=2)[N:22]=[CH:21][CH:20]=1>C1COCC1.[Cl-].[NH4+].O.CCOC(C)=O.CCCCCCC>[Cl:18][C:19]1[C:28]2[C:23](=[CH:24][C:25]([S:29]([N:6]([CH2:5][C:4]3[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[CH:15][C:3]=3[O:2][CH3:1])[C:7]3[S:11][N:10]=[CH:9][N:8]=3)(=[O:30])=[O:31])=[CH:26][CH:27]=2)[N:22]=[CH:21][CH:20]=1

참가 물질

8

반응물 2

HCID 57732216N-(2,4-dimethoxybenzyl)-1,2,4-thiadiazol-5-amineHCID 86687458Perfluorophenyl 4-chloroquinoline-7-sulfonate

생성물 1

HCID 866875714-chloro-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)quinoline-7-sulfonamide수율 82%

시약·촉매·용매 5

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매HCID 8900Heptane용매HCID 25517Ammonium Chloride용매

실험 절차

A flask was charged with N-(2,4-dimethoxybenzyl)-1,2,4-thiadiazol-5-amine (302 mg, 1.204 mmol) and THF (5471 μl) to give a clear solution. The flask was cooled in a dry ice-acetone bath for 5 min, and then a solution of perfluorophenyl 4-chloroquinoline-7-sulfonate (448.3 mg, 1.094 mmol) in THF (1 mL with a 0.5 mL syringe wash) was added drop wise. After 1 h, the mixture was diluted with saturated aq. ammonium chloride, water, and EtOAc, and the layers were separated. The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (40-g Redi-Sep Gold column, 20-70% EtOAc/Heptane) to give an off-white solid. The solid was taken up in heptane and filtered. The collected solid was washed with heptane (2×), then dried under a stream of N2 (g) for 2 h to give 4-chloro-N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)quinoline-7-sulfonamide (426 mg, 0.893 mmol, 82% yield) as a white solid. m/z (ESI) 477.0 (M+H)+.

후처리

  1. customto give a clear solution
  2. temperatureThe flask was cooled in a dry ice-acetone bath for 5 min
  3. customthe layers were separated
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (40-g Redi-Sep Gold column, 20-70% EtOAc/Heptane)
  8. customto give an off-white solid
  9. filtrationfiltered
  10. washThe collected solid was washed with heptane (2×)
  11. dry with materialdried under a stream of N2 (g) for 2 h

출처 및 근거

ORD 기록
ord-fefeabc659fa45ee963eec79e3077c8d
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012443B2

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