Triethylamine → 1-(3-Fluoro-2-(trifluoromethyl)isonicotinoyl)piperidin-4-one

HRID 1617391노트

반응식

HRID 1617391 반응식
[NH:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[F:8][C:9]1[C:17]([C:18]([F:21])([F:20])[F:19])=[N:16][CH:15]=[CH:14][C:10]=1[C:11](O)=[O:12].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[F:8][C:9]1[C:17]([C:18]([F:21])([F:19])[F:20])=[N:16][CH:15]=[CH:14][C:10]=1[C:11]([N:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1)=[O:12]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 337214-PiperidoneHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 265964893-Fluoro-2-(trifluoromethyl)isonicotinic acid

생성물 1

HCID 584313981-(3-Fluoro-2-(trifluoromethyl)isonicotinoyl)piperidin-4-one수율 72.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of piperidin-4-one (1 g, 10 mmol) and 3-fluoro-2-(trifluoromethyl)isonicotinic acid (2.32 g, 11.1 mmol) in DMF (20 mL) were added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (5.62 g, 12.7 mmol) and triethylamine (4.43 mL, 31.8 mmol). The mixture was stirred at room temperature overnight and diluted with EtOAc. The solution was washed with brine, dried with sodium sulfate, filtered and concentrated. Purification on silica gel with 50-100% EtOAc/hexanes gave 2.1 g (70% yield) of the title compound. LC/MS found: 291.2 (M+1)+.

후처리

  1. washThe solution was washed with brine
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification on silica gel with 50-100% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-241777ae01e844a589dd21892e000513
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765734B2

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