1,2-Ethanediamine, N1,N1,N2-trimethyl- → 6-[4-[N-(2-Dimethylaminoethyl)-N-methylaminocarbonyloxy]-2-methoxyphenyl]-5-(5-methylthiophen-2-ylcarbonyloxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline

HRID 1678281Notes

Reaction equation

HRID 1678281 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH2:21][O:22][C:23]([C:25]3[S:26][C:27]([CH3:30])=[CH:28][CH:29]=3)=[O:24])=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13]([CH3:19])([CH3:18])[CH:12]=[C:11]3[CH3:20])=[C:4]([O:31][CH3:32])[CH:3]=1.[C:33](N1C=CN=C1)(N1C=CN=C1)=[O:34].[CH3:45][N:46]([CH3:51])[CH2:47][CH2:48][NH:49][CH3:50]>CN(C)C1C=CN=CC=1.O1CCCC1>[CH3:45][N:46]([CH3:51])[CH2:47][CH2:48][N:49]([C:33]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH2:21][O:22][C:23]([C:25]3[S:26][C:27]([CH3:30])=[CH:28][CH:29]=3)=[O:24])=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13]([CH3:18])([CH3:19])[CH:12]=[C:11]3[CH3:20])=[C:4]([O:31][CH3:32])[CH:3]=1)=[O:34])[CH3:50]

Participants

6

Reactant 3

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 682631,1'-CarbonyldiimidazoleHCID 250156246-(4-Hydroxy-2-methoxyphenyl)-5-(5-methylthiophen-2-ylcarbonyloxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline

Product 1

HCID 248910896-[4-[N-(2-Dimethylaminoethyl)-N-methylaminocarbonyloxy]-2-methoxyphenyl]-5-(5-methylthiophen-2-ylcarbonyloxymethyl)-2,2,4-trimethyl-1,2-dihydroquinolineYield 11%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-(4-hydroxy-2-methoxyphenyl)-5-(5-methylthiophen-2-ylcarbonyloxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 3-2, 42.8 mg, 0.0952 mmol), 1,1′-carbonyldiimidazole (47.7 mg, 0.294 mmol) and 4-dimethylaminopyridine (1.7 mg, 0.014 mmol) was dissolved in anhydrous tetrahydrofuran (1 mL), and then the mixture was stirred at room temperature for 1 hour. N,N,N′-trimethylethylenediamine (25 μL, 0.192 mmol) was added thereto, and then the mixture was stirred at room temperature for 1 hour. The reaction mixture was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (5.8 mg) as a colorless amorphous product. (Yield 11%)

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. customThe reaction mixture was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-c6921928672b416e92ed339621a0d1a0
Source dataset
uspto-grants-2011_08
Patent number
US08008497B2

Reaction notes

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