Pyridine → 8-Chloro-3-(3-methyloxetan-3-yl)imidazo[1,5-a]pyrazine

HRID 245682노트

반응식

HRID 245682 반응식
[Cl:1][C:2]1[C:3]([CH2:8][NH:9][C:10]([C:12]2([CH3:16])[CH2:15][O:14][CH2:13]2)=O)=[N:4][CH:5]=[CH:6][N:7]=1.N1C=CC=CC=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>ClCCl>[Cl:1][C:2]1[C:3]2[N:4]([C:10]([C:12]3([CH3:16])[CH2:15][O:14][CH2:13]3)=[N:9][CH:8]=2)[CH:5]=[CH:6][N:7]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 86674645N-((3-chloropyrazin-2-yl)methyl)-3-methyloxetane-3-carboxamide

생성물 1

HCID 866746468-Chloro-3-(3-methyloxetan-3-yl)imidazo[1,5-a]pyrazine수율 128.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of N-((3-chloropyrazin-2-yl)methyl)-3-methyloxetane-3-carboxamide (1.945 mmol, 0.47 g) in dichloromethane (10 ml) cooled in an ice-bath was added pyridine (27.2 mmol, 2.198 ml) and trifluoromethane sulfonic anhydride (11.67 mmol, 1.971 ml). The ice-bath was removed and the reaction was stirred at room temperature. After 2 hours the reaction mixture was cooled in ice-bath, diluted with ethyl acetate (5 mL) and quenched with aqueous sodium hydrogencarbonate. The organic layer separated and the aqueous layer washed four times with ethyl acetate. The combined organic extracts were dried (sodium sulfate) and concentrated in vacuo. Purification by column chromatography (silica gel, ethyl acetate) yielded 8-chloro-3-(3-methyloxetan-3-yl)imidazo[1,5-a]pyrazine (0.56 g).

후처리

  1. customThe ice-bath was removed
  2. temperatureAfter 2 hours the reaction mixture was cooled in ice-bath
  3. additiondiluted with ethyl acetate (5 mL)
  4. customquenched with aqueous sodium hydrogencarbonate
  5. customThe organic layer separated
  6. washthe aqueous layer washed four times with ethyl acetate
  7. dry with materialThe combined organic extracts were dried (sodium sulfate)
  8. concentrationconcentrated in vacuo
  9. customPurification by column chromatography (silica gel, ethyl acetate)

출처 및 근거

ORD 기록
ord-0e6db191ac6f4b3aadc207f52e251549
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658794B2

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