Potassium Carbonate → 4-chloro-N-[(1R)-1-cyclopropylethyl]-2,5-difluorobenzamide

HRID 571502노트

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HRID 571502 반응식
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[C:16]([F:17])=[CH:15][C:11]([C:12]([OH:14])=O)=[C:10]([F:18])[CH:9]=1.C(=O)([O-])[O-].[K+].[K+].[CH:25]1([C@H:28]([NH2:30])[CH3:29])[CH2:27][CH2:26]1>O.C(Cl)Cl.CN(C=O)C>[Cl:7][C:8]1[C:16]([F:17])=[CH:15][C:11]([C:12]([NH:30][C@@H:28]([CH:25]2[CH2:27][CH2:26]2)[CH3:29])=[O:14])=[C:10]([F:18])[CH:9]=1

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 65578Oxalyl chlorideHCID 27332744-Chloro-2,5-difluorobenzoic acidHCID 7016286(R)-1-Cyclopropylethylamine

생성물 1

HCID 712080524-chloro-N-[(1R)-1-cyclopropylethyl]-2,5-difluorobenzamide수율 96.3%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

Oxalyl chloride (250.0 μL, 2.954 mmol) was added to a solution of 4-chloro-2,5-difluorobenzoic acid (0.0578 g, 0.300 mmol) in dichloromethylene (3 mL), followed by 15 μL of DMF. The mixture was stirred at room temperature for 1 hour. The volatiles were removed under reduced pressure. The residue was diluted with dichloromethylene (5 mL). To the solution was added potassium carbonate (82.9 mg, 0.600 mmol) in water (1 mL), and (1R)-1-cyclopropylethanamine (41.6 μL, 0.450 mmol). The mixture was stirred at room temperature for 30 minutes, and diluted with DCM, washed with water and brine. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to afford the desired product (0.075 g, 96%) which was directly used in the next step reaction without further purification. LCMS (M+H)+: m/z=260.0.

후처리

  1. customThe volatiles were removed under reduced pressure
  2. additionThe residue was diluted with dichloromethylene (5 mL)
  3. stirringThe mixture was stirred at room temperature for 30 minutes
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5ebdac2afb8b4595a4b38c17a76a9f0a
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09023840B2

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