Potassium Carbonate → (S)-N-(alpha-ethylbenzyl)-3-(aminocarbonylmethoxy)-2-phenyquinoline-4-carboxamide

HRID 651060

Reaction equation

HRID 651060 reaction equation
[CH2:1]([C@H:3]([NH:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14]=1[OH:29])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:37][C:38]([NH2:40])=[O:39]>C1COCC1>[CH2:1]([C@H:3]([NH:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:14]=1[O:29][CH2:37][C:38]([NH2:40])=[O:39])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 5311424Talnetant

Product 1

HCID 10836803(S)-N-(alpha-ethylbenzyl)-3-(aminocarbonylmethoxy)-2-phenyquinoline-4-carboxamideYield 50.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.5 g (1.3 mmol) of (S)-N-(α-ethylbenzyl)-3-hydroxy-2-phenylquinoline-4-carboxamide (compound of Description 1) were dissolved, under nitrogen atmosphere and magnetic stirring, in 5 ml of THF; 0.5 g (3.6 mmol) of K2CO3, 0.27 g (1.9 mmol) of 2-bromoacetamide and a small amount of KI were added. The reaction mixture was left overnight under magnetical stirring; the precipitate was filtered off and the residue dissolved in H2O and extracted with EtOAc; the organic layer was washed with sat. sol. NaCl, dried over Na2SO4 and evaporated in-vacuo to dryness. The crude product was triturated with hexane and then recrystallized form EtOH to yield 0.29 g of the title compound as a white solid.

Workup

  1. filtrationthe precipitate was filtered off
  2. dissolutionthe residue dissolved in H2O
  3. extractionextracted with EtOAc
  4. washthe organic layer was washed with sat. sol. NaCl
  5. dry with materialdried over Na2SO4
  6. customevaporated in-vacuo to dryness
  7. customThe crude product was triturated with hexane
  8. customrecrystallized form EtOH

Sources & evidence

ORD record
ord-90f4780e25824ab4a8893ba2340a036b
Source dataset
uspto-grants-2001_08
Patent number
US06277862B1

Linked notes

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