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

HRID 710019ノート

反応式

HRID 710019 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-619b0411ec544e5e9628b1b41a81e9b5
出典データセット
uspto-grants-2015_11
特許番号
US09181226B2

反応ノート

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