Dichloromethane → 7-Chloro-3-(isoquinolin-1-ylaminomethyl)-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester

HRID 1887977Notes

Reaction equation

HRID 1887977 reaction equation
Br[CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([Cl:14])=[CH:9][CH:10]=2)[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:4]=1[C:21]([O:23][CH3:24])=[O:22].C(Cl)Cl.C(N(CC)C(C)C)(C)C.[NH2:37][C:38]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:41]=[CH:40][N:39]=1>O>[CH3:24][O:23][C:21]([C:4]1[N:5]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:6]2[C:11]([C:12](=[O:13])[C:3]=1[CH2:2][NH:37][C:38]1[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH:41]=[CH:40][N:39]=1)=[CH:10][CH:9]=[C:8]([Cl:14])[CH:7]=2)=[O:22]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 737421-IsoquinolinamineHCID 81531DiisopropylethylamineHCID 86672058Methyl 3-(bromomethyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylate

Product 1

HCID 712085397-Chloro-3-(isoquinolin-1-ylaminomethyl)-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl esterYield 7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 10 mL round-bottomed flask, methyl 3-(bromomethyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylate (50 mg, 0.123 mmol) was combined with methylene chloride (5 mL) to give a colorless solution. To this solution, N,N-diisopropylethylamine and 1-aminoisoquinoline were added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into 25 mL H2O and extracted with ethyl acetate (1×25 mL). The organic layer was washed with 1 M HCl (1×10 mL), saturated aqueous NaHCO3 (1×10 mL), and H2O (1×10 mL). The organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 4 g, 5% to 40% ethyl acetate in hexanes), giving 7-chloro-3-(isoquinolin-1-ylaminomethyl)-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (4 mg, 7%). MS calcd. for C27H20ClN3O3 [(M+H)+] 470.1, obsd. 470.9.

Workup

  1. customto give a colorless solution
  2. extractionextracted with ethyl acetate (1×25 mL)
  3. washThe organic layer was washed with 1 M HCl (1×10 mL), saturated aqueous NaHCO3 (1×10 mL), and H2O (1×10 mL)
  4. dry with materialThe organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatography (silica gel, 4 g, 5% to 40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-cb35c4d3acaa4ca685e1feb07576a98c
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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