N,N'-Dimethylethylenediamine → N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)acetamide

HRID 512748노트

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HRID 512748 반응식
CNCCNC.Br[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.[Cl:14][C:15]1[C:19]([NH:20][C:21](=[O:23])[CH3:22])=[CH:18][NH:17][N:16]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu]I.CN(C)C=O>[Cl:14][C:15]1[C:19]([NH:20][C:21](=[O:23])[CH3:22])=[CH:18][N:17]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[N:16]=1

참가 물질

7

반응물 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 122863-BromopyridineHCID 178474372N-(3-chloro-1H-pyrazol-4-yl)acetamide

생성물 1

HCID 118023019N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)acetamide수율 74.3%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

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온도
97.5 °C

실험 절차

A 4-neck round bottom flask was charged with N,N-dimethylformamide (250 mL) and then degassed 2-3 times. Copper(I) iodide (17.9 g, 94.0 mmol) was added, followed by N,N′-dimethylethane-1,2-diamine (16.2 g, 188 mmol) at 25-30° C. The mixture was purged with nitrogen for 30 minutes. 3-Bromopyridine (59.4 g, 376 mmol) was added, followed by N-(3-chloro-1H-pyrazol-4-yl)acetamide (50.0 g, 313 mmol) and potassium carbonate (87.0 g, 188 mmol) at 25-30° C. The reaction mixture was purged with nitrogen for 30 minutes and heated at 95-100° C. for 3 hours, at which point HPLC analysis indicated that the reaction was complete. It was cooled to 25-30° C. and water (1 L) was added over 30-45 minutes. The resulting suspension was stirred at 25-30° C. for 30 minutes and cooled to 0-10° C. It was stirred for 12 hours at 0-10° C. and then filtered. The filter cake was rinsed with water (2×250 mL) and dried to afford an off-white solid (55 g, 74%). Characterization matched sample prepared by previous method.

후처리

  1. customdegassed 2-3 times
  2. customThe mixture was purged with nitrogen for 30 minutes
  3. customThe reaction mixture was purged with nitrogen for 30 minutes
  4. temperatureIt was cooled to 25-30° C.
  5. additionwater (1 L) was added over 30-45 minutes
  6. temperaturecooled to 0-10° C
  7. stirringIt was stirred for 12 hours at 0-10° C.
  8. filtrationfiltered
  9. washThe filter cake was rinsed with water (2×250 mL)
  10. customdried

출처 및 근거

ORD 기록
ord-6baf03ce972f493b83408a8b2ca2e7fa
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102655B2

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