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

HRID 450299

반응식

HRID 450299 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d920efd2a0ee46ad96c21aff13b9a311
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486954B2

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