Tetrahydrofuran → 6-{[6-(1-oxa-5-azaspiro[2.4]hept-5-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl]methyl}quinoline

HRID 16013

반응식

HRID 16013 반응식
[H-].[Na+].[I-].C[S+](C)C.[N:8]1[C:17]2[C:12](=[CH:13][C:14]([CH2:18][N:19]3[C:23]4=[N:24][C:25]([N:28]5[CH2:32][CH2:31][C:30](=[O:33])[CH2:29]5)=[CH:26][N:27]=[C:22]4[N:21]=[N:20]3)=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1.[CH2:34]1COCC1>CS(C)=O>[O:33]1[C:30]2([CH2:31][CH2:32][N:28]([C:25]3[N:24]=[C:23]4[N:19]([CH2:18][C:14]5[CH:13]=[C:12]6[C:17](=[CH:16][CH:15]=5)[N:8]=[CH:9][CH:10]=[CH:11]6)[N:20]=[N:21][C:22]4=[N:27][CH:26]=3)[CH2:29]2)[CH2:34]1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 593418151-[1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl]pyrrolidin-3-one

생성물 1

HCID 593419626-{[6-(1-oxa-5-azaspiro[2.4]hept-5-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl]methyl}quinoline수율 63%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매3회

반응 조건

온도
70 °C

실험 절차

To a flamed dry 3N round bottom flask fitted with a thermometer and condenser was added 95% NaH (69 mg, 2.69 mmol) and anhydrous DMSO (5.0 ml). After stirring for 2 min at R.T. and 70° C. for 45 mins, the reaction mixture was cooled to 3° C. and a solution of trimethylsulfonium iodide (504.1 mg, 2.47 mmol) in DMSO (3.6 ml) was added. After stirring for 30 mins at 3° C., to the reaction mixture, a suspension of 1-[1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl]pyrrolidin-3-one (200 mg, 0.58 mmol) in 1:1 THF: DMSO (16 ml) was added dropwise. After stirring at 0° C. for 3 h, the reaction mixture was poured into an ice cold water (15 ml) and extracted with CH2Cl2 (4×60 ml). The organic layer was washed with brine and dried with MgSO4 and concentrated under reduced pressure. The resulting residue was purified via flash column chromatography eluted with 10% MeOH:CH2Cl2 to give the desired product (130 mg 63%).

후처리

  1. customTo a flamed dry 3N round bottom flask
  2. customfitted with a thermometer and condenser
  3. temperaturethe reaction mixture was cooled to 3° C.
  4. stirringAfter stirring for 30 mins at 3° C., to the reaction mixture
  5. stirringAfter stirring at 0° C. for 3 h
  6. extractionextracted with CH2Cl2 (4×60 ml)
  7. washThe organic layer was washed with brine
  8. dry with materialdried with MgSO4
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting residue was purified via flash column chromatography
  11. washeluted with 10% MeOH

출처 및 근거

ORD 기록
ord-836d0cc1d3fe4067a8acb810c8769456
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732604B2

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