Potassium Carbonate → 2,2-dimethyl-N-(2-methyl-4-pyrrolidin-1-yl-quinolin-7-yl)-propionamide

HRID 2121639ノート

反応式

HRID 2121639 の反応式
I[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[CH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1.[CH3:18][C:19]([CH3:24])([CH3:23])[C:20]([NH2:22])=[O:21].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu]I>[CH3:18][C:19]([CH3:24])([CH3:23])[C:20]([NH:22][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[CH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1)=[O:21]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 12957TrimethylacetamideHCID 113366637-iodo-2-methyl-4-pyrrolidin-1-yl-quinoline

生成物 1

HCID 101718782,2-dimethyl-N-(2-methyl-4-pyrrolidin-1-yl-quinolin-7-yl)-propionamide収率 56.2%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

A suspension of 0.338 mg (1 mmol) of 7-iodo-2-methyl-4-pyrrolidin-1-yl-quinoline, 0.81 g (8 mmol) of trimethylacetamide, 0.414 g (3 mmol) of potassium carbonate (water free) and 20 mg (0.1 mmol) of copper (I) iodide in DMF (10 ml) was heated at 150° C. (oil bath temperature) under an argon atmosphere for 20 h. The reaction mixture was partitioned between EtOAc and water, the layers were separated, the organic layer washed twice with water dried over sodium sulphate and concentrated in vacuo. The residue was applied to silica gel column with CH2Cl2/MeOH/NH4OH (20:1:0.2) as eluent. Combination of the purified fractions and concentration in vacuo gave 175 mg (50.4%) of the desired 2,2-dimethyl-N-(2-methyl-4-pyrrolidin-1-yl-quinolin-7-yl)-propionamide as light brown solid. ISP mass spectrum, m/e: 312.3 (M+1 calculated for C19H25N3O: 312).

後処理

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. customthe layers were separated
  3. washthe organic layer washed twice with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. concentrationCombination of the purified fractions and concentration in vacuo

出典と根拠

ORDレコード
ord-c4b1cd38468c4edd8800f4d292a87e9e
出典データセット
uspto-grants-2004_02
特許番号
US06696467B2

反応ノート

読み込み中…