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

HRID 2121639Notes

Reaction equation

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]

Participants

Conditions

Temperature: 150 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-c4b1cd38468c4edd8800f4d292a87e9e
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06696467B2

Reaction notes

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