Acetic Acid → 5-(1-Benzyl-6-fluoro-1H-benzoimidazol-2-yl)-1,3-dimethyl-1H-pyridin-2-one

HRID 930525노트

반응식

HRID 930525 반응식
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[NH:16][C:17]([C:19]1[CH:24]=[C:23]([CH3:25])[C:22](=C)[N:21]([CH3:27])[CH:20]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=[O:30])C>>[CH2:1]([N:8]1[C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=2[N:16]=[C:17]1[C:19]1[CH:24]=[C:23]([CH3:25])[C:22](=[O:30])[N:21]([CH3:27])[CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

3

반응물 2

HCID 176Acetic AcidHCID 1317351491,5-Dimethyl-6-methylene-1,6-dihydro-pyridine-3-carboxylic acid (2-benzylamino-4-fluoro-phenyl)-amide

생성물 1

HCID 1178894815-(1-Benzyl-6-fluoro-1H-benzoimidazol-2-yl)-1,3-dimethyl-1H-pyridin-2-one

반응 조건

온도
150 °C

실험 절차

1,5-Dimethyl-6-methylene-1,6-dihydro-pyridine-3-carboxylic acid (2-benzylamino-4-fluoro-phenyl)-amide I-12′ (186.000 mg; 0.509 mmol) is dissolved in acetic acid and stirred at 150° C. for 1 h in the microwave. The reaction mixture is then concentrated under reduced pressure and purified on silica chromatography Combiflash (Column: Redisep Rf, 12 g; gradient: DCM/MeOH=100%/0% to 90%/10%; flow rate=30 ml/min; 28 column volumes; detection wavelength: 254 nm). The product containing fractions are combined and concentrated under reduce pressure. The product is then dissolved in acetonitrile:water 1:1 and freeze dried.

후처리

  1. concentrationThe reaction mixture is then concentrated under reduced pressure
  2. custompurified on silica chromatography Combiflash (Column: Redisep Rf, 12 g; gradient: DCM/MeOH=100%/0% to 90%/10%; flow rate=30 ml/min; 28 column volumes; detection wavelength: 254 nm)
  3. additionThe product containing fractions
  4. concentrationconcentrated
  5. dissolutionThe product is then dissolved in acetonitrile:water 1:1
  6. customfreeze dried

출처 및 근거

ORD 기록
ord-3459cfec87fe41e997e0821b5aa6482a
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296748B2

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