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1,4-Dioxane → 5-chloro-3-({4-[(2S)-2,4-dimethylpiperazin-1-yl]phenyl}amino)-6-ethylpyrazine-2-carboxamide

HRID 1526187
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HRID 1526187 반응식
Cl[C:2]1[C:3]([C:11]([NH2:13])=[O:12])=[N:4][C:5]([CH2:9][CH3:10])=[C:6]([Cl:8])[N:7]=1.[CH3:14][C@H:15]1[CH2:20][N:19]([CH3:21])[CH2:18][CH2:17][N:16]1[C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1.C(N(C(C)C)CC)(C)C.O1CCOCC1>O>[Cl:8][C:6]1[N:7]=[C:2]([NH:26][C:25]2[CH:24]=[CH:23][C:22]([N:16]3[CH2:17][CH2:18][N:19]([CH3:21])[CH2:20][C@@H:15]3[CH3:14])=[CH:28][CH:27]=2)[C:3]([C:11]([NH2:13])=[O:12])=[N:4][C:5]=1[CH2:9][CH3:10]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 666174914-[(2s)-2,4-Dimethylpiperazin-1-yl]anilineHCID 848199603,5-Dichloro-6-ethylpyrazine-2-carboxamide

생성물 1

HCID 1176672325-chloro-3-({4-[(2S)-2,4-dimethylpiperazin-1-yl]phenyl}amino)-6-ethylpyrazine-2-carboxamide수율 75.4%

시약·촉매·용매 1

HCID 962
Water
용매

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온도
110 °C

실험 절차

A mixture of 3,5-dichloro-6-ethylpyrazine-2-carboxamide (420 mg), 4-[(2S)-2,4-dimethylpiperazin-1-yl]aniline (392 mg), diisopropylethylamine (665 μL), and dioxane (8.4 mL) was stirred at 110° C. overnight. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic phase was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=95:5) to obtain 5-chloro-3-({4-[(2S)-2,4-dimethylpiperazin-1-yl]phenyl}amino)-6-ethylpyrazine-2-carboxamide (560 mg) as a brown solid.

후처리

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic phase was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=95:5)

출처 및 근거

ORD 기록
ord-d27d009c947c4d899d3e662268493b82
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09085540B2

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