Dimethylcarbamoyl Chloride → 5-(2,5-Dimethyl-pyrrol-1-yl)-2-methyl-2H-pyrazole-3-carboxylic acid dimethylamide

HRID 45150

反応式

HRID 45150 の反応式
[CH3:1][C:2]1[N:3]([C:8]2[CH:12]=[CH:11][N:10]([CH3:13])[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[Li]CCCC.CCCCCC.[CH3:25][N:26]([CH3:30])[C:27](Cl)=[O:28]>C1COCC1>[CH3:25][N:26]([CH3:30])[C:27]([C:11]1[N:10]([CH3:13])[N:9]=[C:8]([N:3]2[C:2]([CH3:1])=[CH:6][CH:5]=[C:4]2[CH3:7])[CH:12]=1)=[O:28]

参加物

6

反応物 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8058HexaneHCID 132489953-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-pyrazoleHCID 178418339Butyllithium

生成物 1

HCID 593947615-(2,5-Dimethyl-pyrrol-1-yl)-2-methyl-2H-pyrazole-3-carboxylic acid dimethylamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3-(2,5-dimethyl-pyrrol-1-yl)-1-methyl-1H-pyrazole (2.0 g, 11.4 mmol) in THF (100 mL) at −78° C., 2.5M nBuLi in Hexane (5.5 mL, 13.7 mmol) is added. After stirring for 1.5 hour dimethylcarbamyl chloride (1.26 mL, 13.7 mmol) is added. After 10 min the ice bath is removed and the reaction allowed to reach room temperature and stir at room temperature for 2 hour before being poured into water, separated, and the water layer extracted with DCM. The organic layers are combined and concentrated. The residue is purified by FCC to give the title compound. MS (ESI) m/z 247.2 (M+1).

後処理

  1. additionis added
  2. customAfter 10 min the ice bath is removed
  3. customto reach room temperature
  4. additionbefore being poured into water
  5. customseparated
  6. extractionthe water layer extracted with DCM
  7. concentrationconcentrated
  8. customThe residue is purified by FCC

出典と根拠

ORDレコード
ord-d9fdb4747b964fbe953eaa34da43b882
出典データセット
uspto-grants-2013_09
特許番号
US08541432B2

関連ノート

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