Cesium carbonate → HCID 58546754, 화합물

HRID 624520

반응식

HRID 624520 반응식
Cl.[NH:2]1[CH2:5][CH:4]([C:6]2[C:11]([Cl:12])=[N:10][CH:9]=[CH:8][N:7]=2)[CH2:3]1.Cl[C:14]1[N:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[Cl:12][C:11]1[C:6]([CH:4]2[CH2:5][N:2]([C:14]3[N:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]=3)[CH2:3]2)=[N:7][CH:8]=[CH:9][N:10]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 740542-ChloroquinazolineHCID 71743784HCID 71743784, 화합물

생성물 1

HCID 58546754HCID 58546754, 화합물수율 47.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
110 °C

실험 절차

2-(Azetidin-3-yl)-3-chloropyrazine hydrochloride (1.50 g, 7.28 mmol), 2-chloroquinazoline (1.20 g, 7.28 mmol, Parkway Scientific), and cesium carbonate (5.22 g, 16.0 mmol, Fluka) were mixed in DMF (30 mL) in a round bottom flask under a nitrogen atmosphere. The mixture was stirred at 110° C. for 17 h. The reaction mixture was cooled to room temperature, diluted with water, and extracted with EtOAc (2×). The combined organic extracts were washed with saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude mixture was purified via silica gel flash column chromatography eluting with 0% to 100% EtOAc in hexanes to give 1.02 g (47%) of a yellow amorphous solid. 1H NMR (400 MHz, chloroFORM-d) δ ppm 4.41-4.50 (m, 1 H) 4.58-4.63 (m, 2 H) 4.65-4.72 (m, 2 H) 7.22-7.28 (m, 1 H) 7.61-7.72 (m, 3 H) 8.28 (d, J=2.35 Hz, 1 H) 8.51 (d, J=2.35 Hz, 1 H) 9.04 (s, 1 H). m/z=298 (M+1).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic extracts were washed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude mixture was purified via silica gel flash column chromatography
  8. washeluting with 0% to 100% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-35a35d305382485599db53b16675eee8
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303028B2

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