Dimethylformamide → Methyl 5-(thiazol-4-ylmethoxy)pyrazine-2-carboxylate

HRID 1526597

반응식

HRID 1526597 반응식
Cl[C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.[S:12]1[CH:16]=[C:15]([CH2:17][OH:18])[N:14]=[CH:13]1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>O>[S:12]1[CH:16]=[C:15]([CH2:17][O:18][C:2]2[N:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=2)[N:14]=[CH:13]1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 406081Methyl 5-chloropyrazine-2-carboxylateHCID 2763215(1,3-Thiazol-4-yl)methanol

생성물 1

HCID 90389321Methyl 5-(thiazol-4-ylmethoxy)pyrazine-2-carboxylate수율 42.2%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
40 °C

실험 절차

A RBF was charged with methyl 5-chloropyrazine-2-carboxylate (1.239 g, 7.18 mmol, Ark Pharm), thiazol-4-ylmethanol (0.8266 g, 7.18 mmol), cesium carbonate (0.689 ml, 8.61 mmol, Alfa Aesar) and DMF (20.51 ml). The reaction mixture was stirred at 40° C. for 3 days. The reaction mixture was allowed to cool to rt and was diluted with water and extracted with EtOAc. The organic extract was washed with water, satd NaCl, dried over MgSO4, and concentrated in vacuo. The crude product was adsorbed onto a plug of silica gel and purified by silica gel flash chromatography, eluting with a gradient of 10% to 100% EtOAc in hexane, to provide methyl 5-(thiazol-4-ylmethoxy)pyrazine-2-carboxylate (0.7606 g, 3.03 mmol, 42.2% yield). MS m/z=252.1 [M+H]+. Calculated for C10H9N3O3S: 251.036. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.89 (s, 2H) 5.60 (s, 1H) 7.86 (d, J=1.96 Hz, 1H) 8.46 (d, J=1.37 Hz, 1H) 8.86 (d, J=1.37 Hz, 1H) 9.14 (d, J=1.96 Hz, 1H)

후처리

  1. temperatureto cool to rt
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel flash chromatography
  8. washeluting with a gradient of 10% to 100% EtOAc in hexane

출처 및 근거

ORD 기록
ord-c0801f5801694ff6a152d83ac632dbb4
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085576B2

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