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

HRID 571502ノート

反応式

HRID 571502 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5ebdac2afb8b4595a4b38c17a76a9f0a
出典データセット
uspto-grants-2015_05
特許番号
US09023840B2

反応ノート

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