Citric Acid → N-[7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl]propionamide

HRID 2113794노트

반응식

HRID 2113794 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]1[CH2:15][CH2:14][CH2:13][C:12]2=[C:16]([NH2:20])[N:17]([CH3:19])[N:18]=[C:11]12.C(N(CC)CC)C.[C:28](Cl)(=[O:31])[CH2:29][CH3:30].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]1[CH2:15][CH2:14][CH2:13][C:12]2=[C:16]([NH:20][C:28](=[O:31])[CH2:29][CH3:30])[N:17]([CH3:19])[N:18]=[C:11]12

참가 물질

6

반응물 4

HCID 311Citric AcidHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 221362787-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-ylamine

생성물 1

HCID 22136285N-[7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl]propionamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

To a stirred solution of 7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-ylamine (5-45; 0.51 g) and triethylamine (0.27 mL) in dichloromethane (40 mL) cooled to 0° C. was added dropwise over 25 minutes a solution of propionyl chloride (0.17 mL) in dichloromethane (10 mL). The resulting mixture was stirred for an additional 1 h at 0° C., followed by 14 h at room temperature. The reaction mixture was stirred with an aqueous 5% citric acid solution (40 mL) for 10 minutes. The layers were separated, and the aqueous layer was further extracted with dichloromethane (50 mL). The combined organic extracts were dried over anhydrous sodium sulfate, decanted from the desiccating agent and concentrated in vacuo. The resulting residue was purified by silica gel chromatography using a dichloromethane/methanol gradient to afford N-[7-(2-chloro-4,6-dimethylphenyl)-2-methyl-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-b]pyridin-3-yl]propionamide (7-6; 0.49 g) as an off white solid: ms (MH+)=347.

후처리

  1. waitfollowed by 14 h at room temperature
  2. customThe layers were separated
  3. extractionthe aqueous layer was further extracted with dichloromethane (50 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  5. customdecanted from the desiccating agent
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-326e8be4b5534630b4ad9660aacfb6ba
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432283B2

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