Triethylamine → 3-chloro-N-(1-(quinolin-2-yl)azetidin-3-yl)pyrazin-2-amine

HRID 2207784노트

반응식

HRID 2207784 반응식
C(N(CC)CC)C.Cl.[N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[N:19]1[CH2:22][CH:21]([NH2:23])[CH2:20]1.[Cl:24][C:25]1[C:30](Cl)=[N:29][CH:28]=[CH:27][N:26]=1>CN(C=O)C.O>[Cl:24][C:25]1[C:30]([NH:23][CH:21]2[CH2:20][N:19]([C:10]3[CH:11]=[CH:12][C:13]4[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=4)[N:9]=3)[CH2:22]2)=[N:29][CH:28]=[CH:27][N:26]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 785752,3-DichloropyrazineHCID 67477378HCID 67477378, 화합물

생성물 1

HCID 772308873-chloro-N-(1-(quinolin-2-yl)azetidin-3-yl)pyrazin-2-amine수율 55%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

Triethylamine (560 mg, 5.6 mmol), 1-(quinolin-2-yl)azetidin-3-amine hydrochloride (557 mg, 2.8 mmol) and 2,3-dichloro-pyrazine (414 mg, 2.8 mmol) were dissolved in DMF (20 mL). The resulting mixture was heated to 90° C. overnight. The mixture was then diluted with water (20 mL) and extracted with EtOAc (2×50 mL). The combined organic extracts were combined and washed with water (20 mL) and brine (20 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (20% to 50% EtOAc in petroleum ether) to give 3-chloro-N-(1-(quinolin-2-yl)azetidin-3-yl)pyrazin-2-amine (479 mg, 1.5 mmol, 55% yield) as white solid. ESI-MS (M+1): 312 calc. for C16H14ClN5 311.

후처리

  1. extractionextracted with EtOAc (2×50 mL)
  2. washwashed with water (20 mL) and brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by flash column chromatography on silica gel (20% to 50% EtOAc in petroleum ether)

출처 및 근거

ORD 기록
ord-0f2503394a03481eb40c7d281707f32a
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376450B2

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