Acetic Acid → N-(2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-3-yl)propan-2-yl)acetamide

HRID 2069867노트

반응식

HRID 2069867 반응식
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17](O)([CH3:19])[CH3:18])=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[C:21]([OH:24])(=O)[CH3:22].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+].C(#[N:37])C>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:12]=[CH:13][C:14]([C:17]([NH:37][C:21](=[O:24])[CH3:22])([CH3:19])[CH3:18])=[CH:15][CH:16]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 594737935-Bromo-3-[5-(1-hydroxy-1-methyl-ethyl)-pyridin-2-ylamino]-1-methyl-1H-pyridin-2-one

생성물 1

HCID 59473804N-(2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-3-yl)propan-2-yl)acetamide수율 34%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

5-Bromo-3-[5-(1-hydroxy-1-methyl-ethyl)-pyridin-2-ylamino]-1-methyl-1H-pyridin-2-one (180 mg, 0.532 mmol) was dissolved in acetonitrile (10 ml). Acetic acid (0.5 ml) was added at room temperature, and then cooled to 0° C. Sulfuric acid, concentrated solution (0.5 ml) was added slowly to the cooled solution. The reaction mixture was allowed to warm up to room temperature after the addition and stirred overnight. The reaction mixture was poured into ice and ethyl acetate was added. Sodium bicarbonate was added slowly to neutralize the acidic mixture and the it was extracted with ethyl acetate, washed with brine and dried over sodium sulfate. The mixture was filtered and concentrated. Crude material was purified by 24 g column with 0-10% MeOH in EtOAc 1:1 Hex to give N-(2-(6-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)pyridin-3-yl)propan-2-yl)acetamide (69 mg, 34%) as a yellow solid. MS (H+)=379.0.

후처리

  1. temperatureto warm up to room temperature
  2. additionafter the addition
  3. additionwas added
  4. extractionthe it was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationThe mixture was filtered
  8. concentrationconcentrated
  9. customCrude material was purified by 24 g column with 0-10% MeOH in EtOAc 1:1 Hex

출처 및 근거

ORD 기록
ord-5dd04e5c06604eda9cabc9371c327991
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299077B2

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