Triethylamine → HCID 12083024, compound

HRID 1168496Notes

Reaction equation

HRID 1168496 reaction equation
Br[CH2:2][C:3](OC(=O)CBr)=[O:4].[NH2:10][C:11]1[CH:12]=[C:13]([CH2:27][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH:14]=[C:15]2[C:20]=1[N:19]=[CH:18][C:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:16]2[OH:26].C(N(CC)CC)C>CN(C=O)C>[N:28]1([CH2:27][C:13]2[CH:14]=[C:15]3[C:16](=[O:26])[C:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:18][N:19]4[CH2:2][C:3](=[O:4])[NH:10][C:11]([CH:12]=2)=[C:20]34)[CH2:29][CH2:30][O:31][CH2:32][CH2:33]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4259817Bromoacetic anhydrideHCID 178469661HCID 178469661, compound

Product 1

HCID 12083024HCID 12083024, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Bromoacetic anhydride (280 mg) is added to ethyl 8-amino-4-hydroxy-6-(4-morpholinylmethyl)-3-quinolinecarboxylate (Preparation 2, 330 mg) in DMF (4.0 mL). Triethylamine (400 mg) is added and the reaction is heated for 10 min at 60° C. After 1 h, the DMF is removed and the product is chromatographed on silica gel with 10% methanol as the eluant to give 310 mg of the title compound as a mixture with triethylamine hydrobromide. Physical characteristics: 1H NMR (DMSO-d6) δ1.40, 2.45, 3.56, 3.69, 4.39, 4.88, 7.49, 7.97, 8.34.

Workup

  1. customthe DMF is removed
  2. customthe product is chromatographed on silica gel with 10% methanol as the eluant

Sources & evidence

ORD record
ord-020301db948b4fa68fa146015877e888
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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