4-Fluoro-3-nitrobenzoic acid → 4-fluoro-3-nitro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-benzamide

HRID 710019노트

반응식

HRID 710019 반응식
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C1C=CC2N([OH:23])N=NC=2C=1.CCN=C=[N:28][CH2:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33].Cl.CCN([CH:42]([CH3:44])C)C(C)C>C(Cl)Cl.O>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:28][CH2:29][CH2:30][CH2:31][N:32]2[CH2:33][CH2:44][CH2:42][C:34]2=[O:23])=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

참가 물질

7

반응물 4

HCID 679874-Fluoro-3-nitrobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 712246724-fluoro-3-nitro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-benzamide수율 90%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-fluoro-3-nitro-benzoic acid (5.0 g, 27.02 mmol) in CH2Cl2 (150 mL), HOBt (6.5 g, 48.63 mmol) and EDC.HCl (6.2 g, 40.53 mmol) were added followed by DIPEA (6.12 mL, 35.12 mmol). The reaction was stirred at room temperature for 6 h. Water (50.0 mL) was added and the layers were separated. Organic layer was washed with brind and concentrated to give crude product 4-fluoro-3-nitro-N-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-benzamide (7.5 g, 90%). This was taken to the next step without further purification.

후처리

  1. customthe layers were separated
  2. washOrganic layer was washed
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-619b0411ec544e5e9628b1b41a81e9b5
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181226B2

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