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

HRID 2069867ノート

反応式

HRID 2069867 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5dd04e5c06604eda9cabc9371c327991
出典データセット
uspto-grants-2012_10
特許番号
US08299077B2

反応ノート

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