2-Methoxyethylamine → HCID 19592849, compound

HRID 613511Notes

Reaction equation

HRID 613511 reaction equation
Br[CH2:2][C:3]1[C:12]2[C:7](=[C:8]([NH:13][C:14](=[O:23])[C:15]3[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:22])[CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][C:4]=1[C:24](OCC)=[O:25].[CH3:29][O:30][CH2:31][CH2:32][NH2:33].C(N(C(C)C)CC)(C)C>C(Cl)CCl.ClCCl>[Cl:21][C:20]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:22])[C:15]=1[C:14]([NH:13][C:8]1[C:7]2[N:6]=[CH:5][C:4]3[C:24](=[O:25])[N:33]([CH2:32][CH2:31][O:30][CH3:29])[CH2:2][C:3]=3[C:12]=2[CH:11]=[CH:10][CH:9]=1)=[O:23]

Participants

6

Reactant 3

HCID 80182-MethoxyethylamineHCID 81531DiisopropylethylamineHCID 19592415HCID 19592415, compound

Product 1

HCID 19592849HCID 19592849, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-bromomethyl-8-(2,6-dichlorobenzoylamino)-3-ethoxycarbonylquinoline (100 mg), 2-methoxyethylamine (18.7 mg) and N,N-diisopropyl-N-ethylamine (134 mg) in ethylene chloride (1 ml) was stirred for 2 hours at ambient temperature. The mixture was diluted with dichloromethane, washed with saturated sodium bicarbonate solution, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (methanoldichloromethane) to give 6-(2,6-dichlorobenzoylamino)-2,3-dihydro-2-(2-methoxyethyl)-1H-pyrrolo-[3,4-c]quinolin-3-one (76 mg).

Workup

  1. washwashed with saturated sodium bicarbonate solution
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by preparative thin layer chromatography (methanoldichloromethane)

Sources & evidence

ORD record
ord-3cd386ab61384507bb2df3569a2464ac
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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