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

HRID 2121639

반응식

HRID 2121639 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

반응 조건

온도
150 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c4b1cd38468c4edd8800f4d292a87e9e
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06696467B2

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