Cesium carbonate → HCID 59447492, 화합물

HRID 1518415노트

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HRID 1518415 반응식
C([O-])([O-])=O.[Cs+].[Cs+].F[C:8]1[N:13]=[C:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:11]=[CH:10][CH:9]=1.Cl.Cl.[S:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N:25]=[C:24]1[NH:32][C:33]([C:35]1[CH:36]=[CH:37][CH:38]=[C:39]2[C:44]=1[CH2:43][NH:42][CH2:41][CH2:40]2)=[O:34]>C(OCC)(=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[S:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N:25]=[C:24]1[NH:32][C:33]([C:35]1[CH:36]=[CH:37][CH:38]=[C:39]2[C:44]=1[CH2:43][N:42]([C:8]1[N:13]=[C:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:11]=[CH:10][CH:9]=1)[CH2:41][CH2:40]2)=[O:34]

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 468355932-Pyridinecarboxylic acid, 6-fluoro-, 1,1-diMethylethyl esterHCID 86644320N-(benzo[d]thiazol-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxamide dihydrochloride

생성물 1

HCID 59447492HCID 59447492, 화합물수율 29%

시약·촉매·용매 2

HCID 311Citric Acid용매HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

Cs2CO3 (831 mg, 2.55 mmol) and 500 mg of 4 Å sieves were dried under high vacuum at 150° C. for 6 hours before the start of the reaction. Once cooled down, compound 120A (100 mg, 0.51 mmol) and compound 1B (327 mg, 0.61 mmol) were transferred to the reaction vessel and the atmosphere was purged with nitrogen. 1.5 mL of anhydrous DMA was then added and the reaction was stirred at 90° C. for 3 hours and then 100° C. for 2 hours. The cooled reaction mixture was then diluted with ethyl acetate and citric acid 10%. The organic phase was washed three times with citric acid, once with water and brine, and dried over Na2SO4. Concentration of the organic phase afforded an orange film/foam. This residue was purified by flash chromatography using SiO2 (AcOEt/Pet. Eth. 0:100 to 40:60). to provide a white solid (72 mg, 29% yield): 1HNMR (ppm, CDCl3) 1.54 (s, 9H), 3.01 (t, J=5.85 Hz, 2H), 4.05 (t, J=6 Hz, 2H), 5.04 (s, 2H), 6.92 (dd, J=8.55 and 0.63 Hz, 1H), 7.09-7.29 (m, 5H), 7.34 (dd, J=7.32 and 0.63 Hz, 1H), 7.60-7.51 (m, 2H), 7.81 (d, J=9 Hz, 1H).

후처리

  1. temperatureOnce cooled down
  2. customthe atmosphere was purged with nitrogen
  3. addition1.5 mL of anhydrous DMA was then added
  4. wait100° C. for 2 hours
  5. customThe cooled reaction mixture
  6. washThe organic phase was washed three times with citric acid
  7. dry with materialonce with water and brine, and dried over Na2SO4
  8. customConcentration of the organic phase afforded an orange film/foam
  9. customThis residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-1600b4021f9d4d74b400fdca7b2d231d
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232273B2

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