Dimethylamine → HCID 66881101, compound

HRID 505205Notes

Reaction equation

HRID 505205 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[C:14]([Cl:15])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[C:8]([CH2:16]Br)[CH:9]=[N:10]2.[CH3:19][NH:20][CH3:21].C(O)C>CN(C=O)C>[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[C:14]([Cl:15])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[C:8]([CH2:16][N:20]([CH3:21])[CH3:19])[CH:9]=[N:10]2

Participants

5

Reactant 3

HCID 674DimethylamineHCID 702EthanolHCID 66882576HCID 66882576, compound

Product 1

HCID 66881101HCID 66881101, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3-bromomethyl-6-chloro-quinolin-5-yl)-acetic acid methyl ester (500 mg, 1.52 mmol) in DMF (10 mL) was added a 33% solution of dimethylamine in ethanol (547 μL, 3.04 mmol). The reaction mixture was stirred for 16 h at room temperature, followed by removal of the solvents in vacuo. The residue was purified by flash column chromatography (silica gel, gradient of CH2Cl2/MeOH 100:0 to 90:10) to afford the title compound as a violet solid (424 mg, 1.45 mmol, 95%). %). 1H NMR (400 MHz, DMSO-d6, 298 K): δ=8.89 (d, J=2.0 Hz, 1H), 8.38 (bs, 1H), 8.00 (d, J=9.1 Hz, 1H), 7.80 (d, J=9.1 Hz, 1H), 4.36 (s, 2H), 3.69 (bs, 2H), 3.63 (s, 3H), 2.24 (bs, 6H). MS (ES+): 293 (M(C15H735ClN2O2)+H)+.

Workup

  1. customfollowed by removal of the solvents in vacuo
  2. customThe residue was purified by flash column chromatography (silica gel, gradient of CH2Cl2/MeOH 100:0 to 90:10)

Sources & evidence

ORD record
ord-1ef44e3afdda432aa092ed9213e0db78
Source dataset
uspto-grants-2010_08
Patent number
US07781438B2

Reaction notes

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