1,2-Dichloroethane → N1-[1-(4-bromophenyl)-2-(1-pyrrolidinyl)ethyl]-N2-(3,4-dichlorophenyl)-N1,N2-dimethylglycinamide

HRID 2114335ノート

反応式

HRID 2114335 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:15][CH3:16])[CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[Cl:17][C:18]1[CH:19]=[C:20]([N:25]([CH3:30])[CH2:26][C:27]([OH:29])=O)[CH:21]=[CH:22][C:23]=1[Cl:24].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:15]([CH3:16])[C:27](=[O:29])[CH2:26][N:25]([C:20]2[CH:21]=[CH:22][C:23]([Cl:24])=[C:18]([Cl:17])[CH:19]=2)[CH3:30])[CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 57418650N-(3,4-dichlorophenyl)-N-methylglycineHCID 57425537[1-(4-Bromophenyl)-2-(1-pyrrolidinyl)ethyl]methylamine

生成物 1

HCID 59809676N1-[1-(4-bromophenyl)-2-(1-pyrrolidinyl)ethyl]-N2-(3,4-dichlorophenyl)-N1,N2-dimethylglycinamide収率 48.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

1-(4-bromophenyl)-N-methyl-2-(1-pyrrolidinyl)ethanamine (4.7 g, 17 mmol) was dissolved in 150 mL of methylene chloride and treated with N-(3,4-dichlorophenyl)-N-methylglycine (4.02 g, 16.6 mmol), EDC (3.5 g, 18 mmol), HOBt (2.47 g, 18.2 mmol), and triethylamine (2.55 mL, 18.3 mmol). The reaction mixture was stirred at room temperature for 18 h. Methylene chloride (50 mL) was added and the reaction mixture was washed with sodium bicarbonate (100 mL) and then brine (100 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was dissolved in 15 mL of DMSO and purified by preparative HPLC (Phenomenex 75×30 mm column, 15 injections, 40 mL/min flow rate, A: 0.1% TFA in acetonitrile B: 0.1% TFA in water, A: 10 to 100% over 15 min, UV detection at 215 nm) to give 4.01 g (48%) of the title compound as a light yellow solid. MS (ES) m/e 500 [M+H]+.

後処理

  1. washthe reaction mixture was washed with sodium bicarbonate (100 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in 15 mL of DMSO
  6. custompurified by preparative HPLC (Phenomenex 75×30 mm column, 15 injections, 40 mL/min flow rate
  7. waitA: 0.1% TFA in acetonitrile B: 0.1% TFA in water, A: 10 to 100% over 15 min

出典と根拠

ORDレコード
ord-85bb6aa6512f48a08e09146610bc7726
出典データセット
uspto-grants-2008_10
特許番号
US07432258B2

反応ノート

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