Picolinic acid → N-Cyclopropyl-N-[1-(pyridine-2-carbonyl)-piperidin-4-yl]-3-trifluoromethyl-benzenesulfonamide

HRID 1428959노트

반응식

HRID 1428959 반응식
[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[N:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[C:51](O)=[O:52]>CN(C=O)C>[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][N:21]([C:51]([C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][N:45]=3)=[O:52])[CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=2)(=[O:6])=[O:7])[CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 1018Picolinic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2773944N-Cyclopropyl-N-piperidin-4-yl-3-(trifluoromethyl)benzenesulfonamide

생성물 1

HCID 24860755N-Cyclopropyl-N-[1-(pyridine-2-carbonyl)-piperidin-4-yl]-3-trifluoromethyl-benzenesulfonamide수율 86%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

N-Cyclopropyl-N-piperidin-4-yl-3-trifluoromethyl-benzenesulfonamide (0.174 g, 0.50 mmol), HOBt (0.068 g, 0.50 mmol), EDCI (0.115 g, 0.60 mmol) and picolinic acid (0.068 g, 0.55 mmol) were dissolved in 5 ml of dry DMF. The mixture allowed to stir at room temperature for 16 hours. The reaction mixture was concentrated to dryness under reduced pressure. Then residue was dissolved in EtOAc (30 ml) and the mixture was washed with saturated NaHCO3 (15 ml) and brine (15 ml). The organic layer was dried over MgSO4 and concentrated to dryness. The crude product was purified through a column of silica gel with a gradient of 0% to 10% MeOH in EtOAc to afford the title compound 7 (195 mg, 86%). The product was taken up in 2 ml of EtOAc. To the mixture, 2 ml of 4 N HCl in EtOAc was added. The solvent was removed and remaining material was the desired product 7 was obtained as a hydrochloride salt (pale yellow solid). LC: 100%. MS: m/z=453.

후처리

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  2. dissolutionThen residue was dissolved in EtOAc (30 ml)
  3. washthe mixture was washed with saturated NaHCO3 (15 ml) and brine (15 ml)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified through a column of silica gel with a gradient of 0% to 10% MeOH in EtOAc

출처 및 근거

ORD 기록
ord-bac9b75a96a34bc7883932cf004de850
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937181B2

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